


Memento Mori

by 7_wonders



Category: American Horror Story: Apocalypse, House of Cards (US TV)
Genre: Alternate Universe - Mob, Blackmail, Blood and Violence, Drugs, F/M, Fluff and Humor, Gangs, Kidnapping, Murder, Organized Crime, Political Alliances, Sexual Content, Sexual Tension, So is Duncan, other various mafia activities, reader's a smartass
Language: English
Status: In-Progress
Published: 2019-10-19
Updated: 2020-12-16
Packaged: 2020-12-23 20:03:49
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 10
Words: 28,099
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21087035
Author URL: https://archiveofourown.org/users/7_wonders/pseuds/7_wonders
Summary: When being in the wrong place at the wrong time lands (Y/N) in the blood-stained hands of D.C.’s most notorious crime boss, Duncan Shepherd, she finds herself unexpectedly in his debt. Perhaps owing the dangerous man a favor would be more torturous if he weren’t so engaging.





	1. King of the Underground

**Author's Note:**

> Here it is! The first chapter of my crime boss Duncan fic. I’m SO excited to share this labor of love with you all, and I sincerely hope that you enjoy it. Feedback is always much appreciated and, if you feel so inclined, I would love if you left a kudos or a comment.

It’s not a route that she would normally take home after classes, but today, (Y/N) (Y/L/N) is running late. The maintenance man is supposed to be at her apartment to fix the kitchen sink in twenty minutes, and it will most assuredly be another week before he can repair it if she doesn’t get home to let him in. This shortcut, through alleyways and past abandoned buildings, is a tour of the dark underbelly of Washington D.C. It’s one that she doesn’t get to dwell on when running late; instead, she walks quickly and clutches her keys in her hand tightly, eyes up and darting back and forth vigilantly. 

After taking this way home twice previously to today, (Y/N) quickly learned which alleys to avoid and which were safer to go down. The alley next to the butcher was safe, the stench of rotting meat causing even the most nefarious of characters to stay away. Bypassing the bridge meant she could dodge the junkies that traded drugs and needles there, and the abandoned set of warehouses were considered too “haunted” and “creepy” for most to venture into. With the rain that drenches the city today and (Y/N)’s lack of an umbrella, these deserted buildings provide the perfect cover as she tries to race home.

(Y/N)’s never seen another person in or around this empty strip, only mice and other small creatures. That’s why it’s so shocking when, as she walks quickly along the back wall, she hears voices from one of the rooms. Ducking behind a wall, she peeks in through a crack in the boards that had hastily been put up to cover a large hole. 

It’s difficult for (Y/N) to comprehend what she’s seeing at first. A man with shaggy hair is on his knees, hands raised pleadingly in the air as he trembles. Others are positioned around the room, blocking exits and providing what she assumes is security. Security for what, she can’t be certain, since the most danger looks to be the man standing above what must be his prisoner. 

“You seem to think that I’m some sort of idiot, Malakai,” the man with the artfully messy brunette hair says nonchalantly, as if he’s discussing the weather. 

‘Malakai’ shakes his head furiously as he stutters, “No, sir, never!” The man in question walks a slow circle around his captive, teeth bared in a savage grin as he takes glee in the scared reaction that he evokes. 

“Hmm, then why did you believe that it wouldn’t get back to me that you were attempting to make deals with people who are determined to take me, and my family, down?” The hostage pales, obviously not thinking he knew. “An amateur mistake; somebody makes a deal, and they foolishly believe that I _don’t_ have eyes and ears everywhere around this city.”

“I-it was an accident, Mr. Shepherd, I promise.” (Y/N) slaps a hand over her mouth, stifling the gasp that threatens to force its way out.

She hasn’t lived in Washington D.C. her entire life, having only moved to the area for school. However, even somebody from the other end of the country would know the Shepherd family name. Although it’s never been said outright, it’s very much implied that the powerful family is involved in more than just politics. Their sudden prominence within the circles of the elite, the roots that spread everywhere, their influence on matters that don’t pertain to politics: it’s easy to make the inference that the Shepherds are involved in some “darker” activities. 

(Y/N)’s heard rumors of what the Shepherd family is capable of. Drugs, weapons, disappearances, murder, and corruption are just the beginning of an extremely long list of grievances. This man, with his hand on his captive’s shoulder and a look that screams revenge, must be the head of the Shepherd family.

“An _accident_,” he teases, reassuming his previous spot in front of the man on his knees. “Unfortunately, you know all too well that we can’t have accidents.”

A gunshot cracks through the air, the bullet quickly and efficiently leaving a hole in the middle of ‘Malakai’s’ head. His eyes roll back into his head slowly as his body slumps forward, blood pooling from the wound on his head. The man who was doing the interrogating, Mr. Shepherd, glances disdainfully down at the blood before stepping back to avoid staining his shoes.

“I’ve told you time and time again that I don’t like a messy job, Langdon,” he calls to someone that (Y/N) can’t see. 

If (Y/N) hadn’t just witnessed a murder, her first time ever seeing someone’s life taken from them, she would stick around to see who he’s talking to. She stumbles back in shock, unable to take her eyes off of the corpse lying on the other side of the repaired wall. Since she’s not looking, she doesn’t see the mouse that scurries over her foot. The shriek of fear that she attempts to hold back isn’t as muffled as she thought it would be under her hand, causing the heads of everyone in the room to snap up as they look for the source of the sound. 

She holds her breath, hoping that the crack she was spying through is too small for somebody to look through if they’re not right up against it. Her heart, along with her hope, sinks when she makes eye contact with the pair of stormy blue eyes belonging to Mr. Shepherd.

“Shit,” he gasps. 

She runs before her brain even realizes what she’s doing, sprinting faster than she can remember running in a long time. Footsteps pound behind her, the echoing sound ironically reminding (Y/N) of gunshots. Once she bursts outside, she immediately searches for an exit that will give her the best chance of evading a horde of murderers. Ducking down, she crawls through a large gap in the bottom of a chain link fence. Those chasing her aren’t deterred, and one quick glance over her shoulder (_stupid_, she thinks, _you’re lucky you didn’t trip over your own feet_) confirms that they’ve decided jumping the fence is easier. 

(Y/N) skids to a stop when she sees that a brick wall blocks her path to freedom. Making a split-second decision, she climbs up onto the dumpster and jumps. Her hands make purchase on the lip of the brick wall, and she summons all of the upper-arm and core strength that she has to start pulling herself up and over. It’s a struggle, and she tries to keep her legs tucked to her chest to prevent whoever’s chasing her from grabbing at her. She’s underestimated how tall these men (or women) are, and shrieks when her nails claw at the brick as she’s yanked down from the wall.

Her head cracks painfully against the pavement as she’s unceremoniously thrown to the ground. Scrambling back on her elbows, (Y/N) stares up at the two burly men who have managed to get her before she could make it over the wall. Hoping that they’ll show her some mercy, she holds up her hands in an ‘I surrender’ gesture. The men look at each other for a moment, as if debating what to do with her, and (Y/N) watches them optimistically.

A swift punch to the face knocks her out.

* * *

She doesn’t jolt awake in one smooth movement, eyes wide and glancing fearfully around. Instead, conscious returns slowly for (Y/N) (Y/L/N). Like pieces of a puzzle being fitted together, the blackness that had enveloped her is replaced, bit by bit, by a state of awareness. She tries to move when she realizes that she’s awake, but her arms refuse. Cold bites at her wrists, the telltale weight of some sort of metal weighing her down. Although her neck aches when she turns her head, protesting after sleeping in such an awkward position, she looks down and notices that she’s handcuffed to a chair.

Blinking quickly to adjust her vision to the shadows that envelop everything, (Y/N) tries to steady her breathing and not panic as she catalogues the room. This definitely isn’t the same room where she saw a man murdered. It’s small, maybe 8x8, and everything’s made of concrete. The walls, the ceiling, the floors: the room looks to be the same flat gray color. A small cart sits in the corner of the room, the only other furnishing besides the chair (Y/N)’s currently bound to. She kicks her legs uselessly, huffing when she sees that they’re bound by rope. Not that her legs being freed would do anything, since the chair is bolted to the floor, but it would still be a bit of a comfort. 

She doesn’t need a mirror to know that there’s blood on her face, probably from the punch that knocked her out. Her nose feels off, like it was broken when she was hit. Maybe it is broken; of course, that won’t matter if she’s killed in this small room. 

Quick footsteps sound in whatever hallway connects to the room (Y/N)’s being held hostage in, making her stare at the door as she tries to figure out what’s going to happen. Will this person save her, free her from her binds and lead her out of this mess? Or will they end her life quickly, using whatever method this mafia decides to be quickest and easiest? 

The bright fluorescent lights flicker on as the door opens, momentarily blinding her. The man that stands before her is tall, his all-black ensemble making him look even more imposing. Two others, a man and a woman, stand behind him (the security detail for these deadly mafia personnel is a little ridiculous). He moves towards her slowly, each move calculated in its fluidity. What scares (Y/N) about this man isn’t the knife that he slowly twirls between his fingers; it’s his cold blue eyes that are completely devoid of any emotion.

His long blond hair, expertly draped over his shoulders, shines as he teasingly drags the flat edge of his knife down her cheek with a chilling smile. “You’ve caused quite a bit of trouble for my boss, are you aware of that?” 

“I promise you that I had no clue what was going to happen,” she says seriously, eyes wide and pleading. 

“That’s funny, all the little mice seem to say the same thing when they’re caught in a trap,” he hisses, tapping her nose harshly to make her wince in pain. “Now, you’re going to tell me who you’re working for, or your nose is going to be the least of your worries.”

“I’m not working for anybody,” (Y/N) insists. He nods as if he understands, but she can tell he’s only humoring her once he rears his hand back and smacks her across the face. 

Her ears ring as her vision whites out for a moment, leaving her unable to hear the cry of pain that rips from her chest. She’s bleeding, that much is obvious. The large rings on this man’s hand must have opened up a couple of cuts on her now-swollen lip. He smirks, tangling his fingers in her hair and yanking her head back. 

“I don’t like to repeat myself, (Y/N).” She doesn’t have time to wonder how he knows her name when she notices the knife he’s holding is now pressed against her chest. “Who do you work for?”

“Nobody, I promise! I was running late to get home–” shit, the maintenance man must be long gone by now, “–and I took a shortcut that I always take when I’m late. I had never seen somebody in that strip of warehouses before, so I stopped to see what was going on. I didn’t know what was happening until that guy got shot.”

“Well then, this must all be one big misunderstanding.”

She nods gratefully. “Yes! Thank you so much, you have no clue–” a searing pain erupts above her eyebrow, and she groans in pain. Her eyesight goes blurry in her left eye, and it’s only when she blinks enough to see the red tint that she realizes she’s bleeding.

(Y/N) watches in disgust as he lifts his stained knife to his lips and cleans the blood off of it with his tongue. He hums delightedly, leaning in close enough that his breath stings the array of cuts. His hot tongue laves at the still-bleeding cut, sampling her blood until it finally clots.

“Mmm, you’re just my type,” he jokes. In the blink of an eye, his amused expression changes to one of anger as he slams his hands on the arms of the chair. “Tell me who you work for!”

“I’ve already told you!” She earns another smack to the face for that, blood dribbling down her chin as she grimaces. 

“Langdon,” a voice sounds from the door that she hadn’t heard open, making (Y/N) jump in her restraints. The man that she saw interrogate his now-dead victim stands behind the blond, a hand rubbing at the stubble on his face. “What did I say about making messes?”

Langdon sighs, rolling his eyes. “But it’s just so much more fun when I get to spill a little blood.” Regardless of his personal feelings, he moves for the door when Mr. Shepherd gives him a pointed look.

(Y/N) glares at Mr. Shepherd as he examines her in silence once Langdon has left. The security, she notices with a sideways glance, remains posted against the door. He fiddles with the sleeves of his expensive leather jacket, and she hopes it’s her defiant look that’s making him show a trait very uncharacteristic to someone who’s supposed to be a mob boss.

“It’s a shame my associate felt the need to bloody up such a pretty face.” He goes to stroke his hand along her face, stopping when (Y/N)’s spit lands on his cheek. Chuckling, he shakes his head. “Now (Y/N), there’s no need to be so hostile.”

“Give me one good reason.”

He doesn’t speak, instead grabbing a key out of his pocket and unlocking the cuffs that bind her hands behind her back. They fall off easily with a quick shake of her wrists as she pulls them forward and rubs at the chapped skin there. Mr. Shepherd takes out a knife and kneels, cutting the ropes tying her feet together. It’s an obvious ploy at attempting to gain her trust, but it’s one that, she reluctantly admits, works. 

He holds out his hand, “Allow me to properly introduce myself. Duncan Shepherd.”

(Y/N) eyes his hand warily, hesitantly shaking it before snatching her hand out of his grip. “I would introduce myself, but you seem to already know who I am.” She falters when Duncan Shepherd sheathes his knife, thrown off by this sudden change. “You’re not…going to kill me? Or you are, just not with that.”

“It wasn’t at all difficult to find out everything about you from a few simple background checks. I figured, either you’re telling the truth or you’re the worst informant my enemies have hired yet.”

“You couldn’t have checked my identity before you sent your goon to rough me up?”

“I apologize for that, but it’s just protocol. As you may imagine, my profession leaves very little room for leeway.” Duncan smiles at her, setting his hands on the arms of the chair in the same way that Langdon did mere minutes before. “You do know what my profession is, don’t you (Y/N)?”

“Vaguely,” she says dryly, peeved at how he insists on repeating her name. “I’m not too acquainted with the sort of business you’re involved in.”

“So I heard,” he smirks. (Y/N) tries to steady her thumping heart, which had decided it was off to the races when Duncan’s eyes, which she could see now were varying shades of dark and light blue that created a hypnotic combination, twinkled in the fluorescent light and his smile showed off the slight dimple on his cheek. _How pathetic of me, just because he’s cute doesn’t mean he’s not a mafia boss_. “You really shouldn’t take shortcuts through notoriously bad areas. You never know what kind of trouble you could get into.”

“Oh, I think I have a pretty good idea.”

Duncan stands up straight, allowing (Y/N) to feel slightly more comfortable now that she’s not directly breathing the same air as he is. Frowning slightly, he turns to the security posted at the door and mutters something, the woman nodding and disappearing out of the door. (Y/N) and Duncan remain silent until she returns, a bowl of water and a clean towel in her hands. Taking the supplies from her, Duncan wrings the towel out and holds it out as an offering.

“Either you clean yourself up or I do it for you,” he says when he senses her reluctance, waiting expectantly until she finally gives in and grabs it from him. He watches her closely, examining every wince she makes as she tries to clean the blood off of her already-bruising face. “Hmm, now what do we do with you?”

The blood rushes out of (Y/N)’s face as her heart drops. “What do you mean? You know I’m telling the truth, so let me go.”

“I could do that, but you did witness a murder. Who’s to say that you won’t run to the police the second I let you walk outside?”

She wants to deny it and emphatically say that she would never do that, but they both know that would be a lie. _Out of the frying pan and into the fire,_ (Y/N) thinks bitterly.

“The obvious answer, of course, would be to just kill you.” Duncan looks at her, taking pride in how she doesn’t even attempt to hide the fear on her face. “However, I believe you’ll be much more useful alive than dead.”

“‘Useful’ how?” Everything she’s seen in movies and TV shows about the mafia has her mind racing with the worst possible thoughts.

He ignores (Y/N)’s question, choosing instead to pull himself to his full height in some sort of a power move. “Prove to me that you won’t go to the authorities, and this whole matter will be forgotten.”

“How am I ever supposed to prove that to you?” (Y/N) asks hopelessly. 

He shrugs. “We’ll find something that benefits the both of us.” At the horrified look on her face, Duncan shakes his head quickly. “No, nothing like that. I may be the head of one of the most influential families in Washington D.C., but I’m still a gentleman.”

“So then…”

“Think of it like running errands. Collecting dues, running product, gathering information on my behalf. You’d make a good little spy if you had the right training.” He goes to touch (Y/N)’s cheek, and she smacks his hand away belligerently.

“Don’t,” she warns. Duncan takes a step back, holding his hands up to teasingly show his harmlessness before he folds them behind his back.

“My associates will be in touch when we get something worked out.”

“Wait!” 

Duncan ignores her call, instead motioning to his security to open the door for him. Before he makes his exit, he whispers something to the male guard. With one last nod of acknowledgement in (Y/N)’s direction, Duncan leaves her alone in the room again. This time, her vision isn’t cut off with a punch; it’s with a black cloth bag forced over her head.


	2. To Fight the Powers that Be

**Summary for the Chapter:**

> Duncan Shepherd decides that, before he makes (Y/N) prove that she won’t go to the police about the crimes she’s witnessed, he needs to teach her a bit about defending herself.

**Notes for the Chapter:**

> Chapter 2! I know it's been a while since I posted the first chapter, but that's a part of being a college student. Kudos and comments are very much appreciated, and you can find more of my work on Tumblr @7-wonders.

In the three days since (Y/N) had been abruptly dumped in the living room of her apartment after being kidnapped, she had gotten a total of ten hours of sleep. It wasn’t that she was scared of the Shepherd family; no, she was downright _terrified_. Her eyes burned from a lack of sleep, her stomach churned from all of the caffeine she had forced down her throat, and her mind raced with paranoid thoughts at every unfamiliar sight and sound she encountered. Any person she hadn’t seen before, any sound she hadn’t heard before, anything that looked out of place, immediately had her spine stiffening and her heart thumping.

Her friends and coworkers had all been extremely concerned when she showed up in public with bruises of varying shades and a noticeable cut above her left eyebrow. She had been able to convince them that she had been jumped on her way home the other night, but that only served to have everyone try and contact the police on her behalf. Frantically, (Y/N) had to think quickly and say that the police had been contacted and that they were being careful due to the possibility of this being related to gang activity; a half-lie. They had still been worried, of course, but were willing to acquiesce now that they believed the authorities were involved. What they didn’t know wouldn’t hurt them–it’s what they _did_ know that would hurt them.

(Y/N) couldn’t decide if Shepherd and his goons not showing up yet was a good thing or a bad thing. Maybe they had finally come to their senses and decided that she’s not actually a threat to their massive crime syndicate. They could also simply be laying in wait, biding their time for the perfect moment to kill her and make it look like an accident. It seems far more likely, however, that they’re just enjoying drawing out the wait and making her squirm. 

Opening the door to her apartment, (Y/N)’s immediately aware that something is wrong. The door leading to her bedroom is closed, and she’s certain that it was open before she left this morning. A sensible person would backtrack out of the apartment and call the police, but a sensible person also doesn’t get wrapped up in mafia dealings. If (Y/N) calls the cops and it does turn out that whoever’s in her apartment has been sent by Duncan Shepherd to kill her, there’s no telling what would happen to her loved ones and herself, provided she survive fighting off a trained assassin.

Quietly opening the closet door to her left, (Y/N) grabs the baseball bat her father insisted she keep handy in case of intruders. At the time, she had rolled her eyes and made fun of it, but now she’s thankful she had listened. She’s grateful that the door doesn’t bang against the frame, or that the handle doesn’t make a sound when she releases it. 

(Y/N) holds her breath as she creeps closer to her bedroom, the bat clutched tightly in her hands and held up like she’s ready to swing at a pitch. She can’t help but feel a bit like the cliche “final girl” in a horror movie, bravely, yet stupidly advancing towards the danger that lies straight ahead. Stepping over a part of the floor that she knows is capable of creaking loudly, (Y/N) feels a surge of adrenaline rush through her now that she’s right outside of the door. It’s open just a crack, and hearing rustling from inside confirms her fears that someone had broken into her home.

_Deep breath_, (Y/N) thinks, closing her eyes and attempting to gather up enough courage to actually go in and face the intruder head-on. Her grip on the bat tightens, and she starts to count to three.

_1…_she moves her knee against the door.

_2…_she opens her eyes and steadies herself.

_3…_she kicks the door open with a gusto.

Without giving herself time to think, (Y/N) charges into her bedroom with her weapon at the ready. The room’s dark, so she can’t see who is here with her, but she does see that it’s someone tall and broad-shouldered. She immediately swings for the person’s head, but they’re faster than she is. 

Within seconds (Y/N)’s disarmed and pinned up against the wall, an arm over her shoulders and a hand over her mouth. She’s breathing heavily, shaking from the fear that death is now imminent, when she finally realizes that the blue eyes she’s staring into are Duncan Shepherd’s blue eyes.

“You’re not going to scream if I remove my hand, now, are you (Y/N)?” his silky voice cuts through the air. He’s satisfied when she shakes her head as far as she can with the limited mobility that being caught in Shepherd’s grasp allows, and pulls his hand away from her face. “Good girl.”

(Y/N) scoffs and attempts to push him off of her, but is disheartened to find that he barely budges. “It’s rude to break into somebody’s house, you know. You could have at least called ahead.”

“I’ll remember that for next time.”

“How did you even get _in_ here?” The moment she asks the question, she knows the answer. Choosing to avoid his smug retort, she keeps talking. “For a mafia boss, you’re not very stealthy.”

“Trust me, if I didn’t want you to know I was here, you wouldn’t.” She wants to call his bluff, but the look that he’s giving her lets her know that he’s completely serious. “Nice little place you’ve got here, by the way. It’s…comfortable.”

“What do you want, Duncan? I’m guessing you didn’t come here to make small talk.”

“You’re correct.” He releases his hold on her, and she breathes deeply at the sudden lack of a weight over her chest.

“Need me to run drugs? Go…” she racks her brain, trying to think of what a man like him would need from someone like her, “go and rough somebody up?”

Duncan chuckles, picking up a photo on (Y/N)’s dresser of her and her parents at her high school graduation and looking at it idly. “I actually was going to give you your first assignment, but then I realized: you’ve had absolutely no sort of training whatsoever, self-defense or otherwise. I may be cruel, but I’m not cruel enough to throw somebody into the lion’s den completely unprepared.”

“I know loads of self-defense!” (Y/N) yelps when Duncan crosses the room quickly and grabs her wrist, pulling her arm straight, and examining her palm.

“No, you don’t. Look at you,” Duncan mutters, lightly tracing over the planes of her hand, “these are not the hands of someone who’s fought before.”

“I’ve been in fights before!” A lie, but she might as well run with it now that she’s gone this far.

“Don’t lie to me, (Y/N). You’re lucky that I decided to stop by instead of Langdon; he doesn’t tolerate liars.” A chill runs up her spine at the thought of that horrendous man.

“If you only came here to make fun of me, I’d rather you just kill me instead.”

“Now, that’s not the _only_ reason.” Duncan lets go of (Y/N)’s hand and walks out of her bedroom, leaving her standing utterly confused.

“Wh-where are you going?”

“I’m going to teach you how to defend yourself, of course.” He looks behind his shoulder at her, a small smile on his face. “Are you coming or not?”

* * *

She hadn’t been expecting Duncan to take her to an elaborate gym tucked in the middle of the city, but she hadn’t been expecting most events that had happened to her lately. “You own this, then?” (Y/N) asks, following Duncan through the deserted lobby. 

“Technically, no. However, the owners of this business have a contract with my family, where we invest in the business and make sure that there’s no competition in this area in exchange for a cut of their profits and use of the property however we see fit.”

(Y/N) wrinkles her nose. “All illegal, I’m guessing?” Duncan remains silent, but the smirk playing on his lips tells her that she’s right on the nose. “So what sort of self-defense are you going to teach me today?”

“Nothing too strenuous, don’t worry.” She comes to a stop at a door marked ‘private,’ Duncan entering a password on the keypad and pressing his hand to the screen that opens up underneath the keypad. The LED light blinks green and a mechanical hissing signify the unlocking of the door, which Duncan quickly opens. “Today, we’ll most likely just work on weapons training.”

“There’s an entire shooting range back here!” (Y/N) notes in awe, taking in the sight of a large gun range behind the inconspicuous door that they came through. Upon realizing that Duncan’s already walked ahead of her and is unlocking a large cabinet, she hurries to catch up to him.

“You’ve never held a gun before,” Duncan notes, opening the cabinet to reveal a large arsenal of guns. All different models, sizes, types; (Y/N)’s pretty sure that if there’s a gun that’s been manufactured before, the Shepherd family owns it. 

“I–”

“Don’t try to deny it. I could tell the moment I looked at your hands earlier.” When she quirks a questioning brow, Duncan elaborates. “You don’t have any sort of calluses on your trigger finger, or where your hands would rest against a gun.”

“I have to admit, I’m pretty impressed at what you can tell just from looking at a person’s hands.”

He chuckles, looking through his catalogue’s worth of guns before grabbing one off of the wall. It’s a handgun, that much she’s certain, but she doesn’t know anything else about the weapon beside that. “This is a Glock.” Duncan holds out the gun to (Y/N), who nods.

“I have no clue what that means.”

“It’s the type of gun.”

“So I’m guessing it’s a good gun?”

“Yes, it’s an extremely good gun.” He notices how apprehensively she’s staring at it and sighs. “Lesson number one: don’t be afraid of the gun. It’s not going to do anything that you don’t want it to. _Especially_ when it’s not loaded.”

(Y/N) bites back a mean-spirited comment. “I’m not _afraid_ of the gun, I’m just not quite sure what I’m supposed to do with an unloaded gun.”

“We’re going to load it.” Pressing a small button on the side, a piece of the gun slides out of the bottom while the top slides back. “This is the magazine, where the bullets are stored. Typically, any gun that you receive will already be loaded, but it’s good to learn how to load a gun.”

He hands her the empty magazine and sets a box of bullets on the table, watching with a skilled eye as she examines the shiny lead pieces. Picking one up, she holds it between her fingers and rolls it around in her palm before putting it in the magazine. “Like that?”

“Yes, perfect.” She repeats her actions until 13 rounds have been loaded. “Now load it back into the gun. Don’t be soft about it, you need to do it quickly so you can hear it click into place.”

This part’s a little more difficult, but she still manages to get the magazine back into the gun. “What do I do now? The top part is still out.”

“Hand me the gun.” (Y/N) does as she’s told, and watches as Duncan handles the weapon like he’s had a gun in his hand from the moment he was born. “Racking the slide back is tricky, as it’s really easy to get your hand pinched when the slide goes back into place.”

She holds her breath as the gun does exactly as he said it would, sliding back into place harshly. If she had been the one to do that, it’s almost a guarantee that she would now have an injured hand.

“Don’t ever point a gun at anything unless you’re prepared and willing to shoot. Hopefully, it will not come to you ever having to actually shoot, but just pointing it at a person takes an extraordinary amount of willpower.” 

Duncan presses a small piece next to the trigger, which (Y/N) figures with her limited amount of firearm knowledge to be the safety. Gripping the gun with one hand, he lifts his arm and points the weapon at a target with the silhouette of a person on it across the room. He doesn’t even have to look through the sight before he fires, staring down the range and delicately pulling the trigger a millisecond after (Y/N) claps her hands over her ears. The gun fires twice, one bullet striking the chest, and the other striking the head.

“Now it’s your turn.” Duncan turns the safety back on before he gives the gun back to (Y/N), and she attempts to mimic the stance that he had assumed when shooting.

The gun feels even more foreign in her hand now, the metal still slightly hot from recently being fired. It’s heavy, and it doesn’t feel right as she holds it like Duncan had. Looking over at him with a frown, no words are necessary when her face expresses her displeasure.

“May I?” Duncan asks, gesturing to her hands. (Y/N) nods, and Duncan moves behind her. “Your grip is too tense,” he mutters, gently adjusting her grip on the gun. 

“Wasn’t aware you could hold a gun too tightly.”

“It affects the trajectory of your bullet, miss know-it-all.” He takes a step back to look over her stance, nodding to himself. “Now place your other hand on the bottom of the gun. You’ll want some more force to keep the gun from recoiling too hard on your first time shooting.”

“I can’t hold it with one hand like you did?”

Duncan shakes his head. “Just–shoot, and you’ll see why you need two hands.” Taking a deep breath, (Y/N) clicks off the safety just as Duncan had and stares down the room at the target against the other wall. 

She’s not sure what she thought shooting a gun would be like, but whatever her imagination had decided was nothing when it came to actually shooting the gun. The moment she pulls the trigger, the gun jumps in her grasp, and she has to hold on even tighter to keep it from flying out of her hands. The sound of the gun going off reminds her of a small cannon, and her ears ring from the proximity. There’s not a third hole to join the previous two on the picture of the target, which means she completely missed.

“Holy shit,” she breathes, shakily turning the safety back on before setting the gun down on the table.

“Told you that you’d need both hands on the gun.” Duncan tries not to sound smug, but that’s impossible when the regular tone of his voice is smug.

“I didn’t think it’d do _that_!”

Duncan bites his lip to keep from laughing. “Come on, try it again. I want to at least see you hit the target before we’re done.”

Although (Y/N) eyes him warily, she still picks up the gun and resumes the same stance. This time, she’s a little more prepared when she fires, but she still manages to completely miss the target as she puts most of her focus on keeping the gun from jumping.

“It’s useless to try and teach me.” She scrunches her nose, trying to get rid of the ringing in her ears. “I’m not going to hit that stupid target, and if things go the way I’m hoping then I won’t even have to pull a gun on someone.”

“But if it does come to that, wouldn’t you want to have some sort of assurance that you will at least hit somebody if you need to shoot them?”

“Yes,” she admits begrudgingly. 

“Is it alright if I help you, then?”

“Yeah, sure.” (Y/N) watch Duncan closely as he moves behind her again. “Just–no funny business, mister.”

He huffs out a laugh, but nods. “Eyes on your target,” he mutters into her ear.

Duncan’s chest rests against (Y/N)’s back as his arms loop around her, coming to rest on top of her hands. (Y/N)’s breath hitches, imperceptibly to most, but to someone with the ability to read people like a seasoned FBI agent, that small tic of emotion is clear as day to Duncan. Laying his chin on her shoulder, he lifts the gun, and her arms, up to point at the target.

“The key,” he says quietly, his chest rumbling with the vibrations of his voice, “is _when_ you shoot. People think that the way they breathe doesn’t affect the shot, but it does. You want to pull the trigger when you exhale.”

(Y/N)’s shoulders are tense as she tries not to think about the dangerous crime boss that could easily kill her with the position they’re both currently in. “Okay, shoot on the exhale. Got it.”

“Look through your sight on the exhale before you shoot, that way you can get a feel for where you’re shooting.”

“Pretty sure I won’t have enough time to do all this when there’s some goon coming at me with the sole objective to kill me.”

“It becomes much easier after you’ve practiced a few times.”

“Like riding a bike,” she mutters.

“Pick where you’re going to shoot.” He redirects her attention to the task at hand. (Y/N) aims for the chest, where Duncan had first shot, and desperately tries to keep her hands steady. “Ready?”

“I think so.” She’s not ready, but there’s no time like the present, so she tries to convince herself as well as Duncan of the opposite.

Duncan places his trigger finger over hers. “Breathe in,” he commands, breathing in with her so she has no choice but to follow. “Out, and shoot.”

As (Y/N)’s shoulders come back down with an exhale, Duncan waits until he feels the muscle of her trigger finger start to tense as she pulls the trigger, only moving when she does. The gun moves far less than it has previously, another set of hands helping to keep it in the position that it’s supposed to be in. (Y/N) still twitches a little bit when she shoots, and the bullet doesn’t land where she planned for it to be. Instead, it’s a few inches up, hitting the target in the side of the neck. 

“Damn,” she mutters, relaxing back into Duncan’s grasp without noticing she’s doing so, “really thought I had that.”

“It was much better than last time,” he reassures her. “After all, you actually hit the target.”

(Y/N) cranes her head back to glare at him, the smile on her face betraying her. “Rude,” she admonishes. 

The smile on her face freezes when she realizes that she’s still wrapped in Duncan’s arms, the man awkwardly clearing his throat and unwrapping his arms from around her. She looks ahead at the target, anything to avoid looking him in the eyes.

“I think that’ll be good for today, now that you’ve at least held and shot a gun.”

“Yeah, that’s–that’s a good idea.” She walks towards the wall, grabbing the bag she had hastily snagged on her way out of her apartment. “Are my ears always going to ring like that?”

Duncan shakes his head. “No. Eventually, you’ll get used to the sound.”

“Great. Cool.” She bobs her head, trying to think of something else to say. “Um, see ya around, I guess?”

“Have a good night, (Y/N).” She nearly rushes out of the door as soon as Duncan makes it clear he’s done with her for now, waiting until the cool evening air hits her face outside to process what had happened.

“Fuck. Fuck, fuck, fuck,” she whispers, running a hand through her hair as she walks quickly down the sidewalk.

(Y/N)’s not going to let herself get flustered from minor physical contact. She’s stared death in the eye now; there’s no reason to get nervous about the leader of a mob teaching her how to shoot. Still, she finds herself haunted by Duncan Shepherd for the rest of the night, his scent lingering on the air, his touch still ghosting along her skin, and his eyes haunting her in her dreams.


	3. Money, Power, and Glory

**Summary for the Chapter:**

> The sordid history of Duncan’s rise to the top, and hand-to-hand combat lessons that lead to other activities.

**Notes for the Chapter:**

> Hello and welcome to another chapter of Memento Mori! I hope everyone’s had a fantastic holiday season. As my belated gift to you all, this chapter includes what everyone’s been waiting for: SMUT. As always, if you enjoyed this, I would love if you left a kudos or a comment. Happy reading!

By all accounts, Duncan Shepherd is not a man known for showing emotion, unless that emotion is sadistic pleasure gained at the expense of others’ well-being. Nobody would describe Duncan Shepherd as patient or helpful, a gentleman or a teacher. Instead, Duncan Shepherd is often referred to as cruel, vicious, heartless, and bloodthirsty, to name a few. But most of all, Duncan Shepherd would not be described as weak. 

Duncan’s proud of the reputation that he’s cultivated through his few short years as the official “head” of the Shepherd family. However much he hates to acknowledge it, he has his strict upbringing to thank for that. 

An absent father who died when Duncan was barely old enough to walk, followed by rumors that the supposed grieving widow was the one who ‘accidentally’ gave her husband too many sleeping pills mixed with a hearty glass of aged bourbon with the endgame of joining her brother and building the Shepherd name into one of the most powerful monikers in Washington D.C. Being passed off from nanny to nanny, his mother and uncle too busy climbing their way up the elitist ladder to take care of the sole heir to the elaborate empire they were crafting. 

The Shepherd family had always been wealthy, but the wealth became exorbitant upon Annette and Bill’s foray into the underbelly of the city’s privileged class. Suddenly, Duncan was shipped off to the best boarding school in North America, with business and political skills instilled in him from the very beginning of his enrollment at the Andover Preparatory School (along with how to dodge punches and how to go on a coke binge and still show up for your 8 a.m. looking none the worse). Prep school was difficult, but it was much more preferable than being around his uncle.

Duncan’s met a lot of douchebags through his close association with the GOP, but Bill Shepherd embodies toxic masculinity. For a man so fond of collared shirts and quarter zip pullovers, he knew just how to emasculate even the most confident of men with a few well-shot insults. For his detested nephew, however, “a few” insults was a daily occurrence that could be counted on with the regularity of the rise and fall of the sun. The physical aspect of Bill’s temperament, slapping and punching and the feeling of his fingers digging into Duncan’s jaw as he commands him to “ _ use your empty, good-for-nothing brain and just  _ listen  _ to me, god damn it _ ,” marred Duncan’s late teen years. 

His uncle saw him as a threat. Even if Duncan wasn’t able to discern that himself from the increasing beatdowns, whether physical or verbal, as he reached adulthood, his mother was sure to remind him of that fact whenever he was younger and would come crying to her about the mean things that Uncle Bill had said to him. If he closes his eyes, he can still feel her hand carding through his light brown locks and her soft voice reminding him that everything under the control of the Shepherd name would be his one day, regardless of what her brother said. She never confronted Bill about the abuse, but she had tried, in her own fucked-up way.

Ultimately, Duncan has Bill to thank for his rise to the top of the Shepherd Freedom Foundation, Gardner Analytics, Shepherd Unlimited, and, of course, the Shepherd family itself. It was Bill who accosted Duncan after the young Shepherd had gotten into a gunfight with a rival group that had attempted to blindside him on his first solo meeting to restake territory claims over the different wards of Washington D.C. It was Bill who grabbed Duncan by the collar of his bloodstained black shirt, throttling him and bitterly spitting out that he would never be a “true” Shepherd. It was Bill who took a swing at Duncan, a horrified Annette frozen with fear across the room.

And, in the end, it was Bill who was too slow to react to Duncan pulling a knife out in retaliation and jabbing it into his uncle’s abdomen. Annette had screamed, but Duncan had hardly heard her over the sound of his blood roaring in his ears as he stared at his hands, soaked in the blood of his uncle who was on the floor and gasping for his last breaths. Duncan’s Goliath was finally slain, dead on the floor with blood slowly spilling out from the stab wound. His first murder had been his most difficult, and while the easiness of ending somebody’s life scared him, the fact that Duncan enjoyed killing his uncle frightened him the most.

It had been all too easy to frame Bill Shepherd’s death as a robbery-gone-wrong. Annette, already shaken from seeing her brother stabbed to death by her son, had been able to pull on years of experience with lying through her teeth to recount to police the harrowing ordeal of how she came to the building that housed the various Shepherd businesses only to see Bill bleeding out in his office. With the notability of the victim and the million dollars that had been stolen from the busted safe behind the bookshelf (in reality, the money was funnelled into one of the family’s many offshore accounts, but that was neither here nor there), the case was textbook open-and-shut.

The “grieving” Shepherds had publicly vowed that their figurehead’s death would not be in vain. They would build on his legacy, just as he would have wanted. Behind closed doors, Annette had begrudgingly admitted that Duncan was in the right when he shoved a blade into Bill’s stomach, especially upon seeing just how capable of leading Duncan was. More money, more power, more territory, more influence: the more the Shepherd family became a name at the forefront of every conversation about the VIPs of Washington D.C., the more determined Duncan was to reach the top. He would stop at nothing to be better than his uncle, to prove to him one last time that he was more of a man than Bill Shepherd, cold and rotting six feet under, could ever be. 

So maybe people are right when they refer to Duncan Shepherd as a callous, cruel, bloodthirsty, monster of a mob boss. But Duncan is certainly not  _ weak _ .

Why, then, does he feel so weak when he’s around (Y/N)? The woman shouldn’t even warrant a passing thought, not when Duncan has far more important matters to be dealing with. He should have killed her; it would have been far easier, and created less of a lasting effect (for Duncan, at least). Yet, when he heard about how she nearly scaled a wall when attempting to run from some of his men, and when he saw the fire blazing in her big eyes as she spit at him when he tried to touch her face, he knew he couldn’t.

Duncan’s found it impossible to stop thinking about last week’s shooting lesson. How she looked to him for guidance on what, to Duncan, is the most basic of tasks. Her defiant comments that make him angry while simultaneously making him chuckle. Her wide smile when she hit the target. The smell of her hair as Duncan loomed behind her to check her sight.

The way that her body slotted perfectly against his when he closed his hands on top of hers.

Duncan’s stirred out of his unusually soft reverie by the chiming of his phone. An email notification from one of his tech employees shows on the screen, the subject line warning him of an extended search of his name and family in the metropolitan area. It may sound conceited, but any search taking place within a 30 mile radius lasting longer than a few minutes carries with it the potential of a threat against the empire that Duncan has so carefully built. He’s sure it’s nothing, but clicks on the email just to be certain.

His eyes scan quickly over the contents of the message, noting the IP address and the approximate length of said search. The IP address traces back to a physical residence, the location of which makes Duncan smirk. It’s (Y/N), and he has no doubt that he’s been on her mind just as much as she’s been on his. Finding her file (because of course Duncan Shepherd is going to have an extensive file for every person he’s ever interacted with) on his computer, he types her number into his phone and sends her a short text.

_ “Training tomorrow, 3 p.m., same location as last week. Oh, and the next time you’re interested in learning more about me, you need only ask. -D.S.” _

//

The embarrassment of knowing that Duncan Shepherd knew that (Y/N) was searching for information about him still controls her emotions as she readies herself to once again meet the notorious mob boss. She thinks she would rather die than see the triumph that sparkles in his crystal blue eyes of the knowledge that she cannot stop thinking about him. 

In (Y/N)’s defense, it was merely an informative search. Not being from the area, she figured that it would be a good idea to learn a little bit more about the man she is now indebted to for the foreseeable future. What she had learned was sad and brutal, but also what she expected. Wikipedia described a rich boy who was coddled until he was old enough to receive a position at the top of one of his family’s companies, while the gossip tabloids loved to speculate on the true amount of wealth that the family possesses. Forbes Magazine called him a bright, young entrepreneur whose tenacity was forged out of the tragedy of his uncle’s murder, and the Washington Herald painted a compelling narrative of various criminal activities and how they lined up with events in the rise of the Shepherd family.

(It’s probably no coincidence that, shortly after the three-part investigative story had been released, the Herald’s editor-in-chief, Tom Hammerschmidt, was found floating face-down in the Potomac river with a bullet lodged in his head. The official cause of death was ruled a suicide, but the popular rumor is that a furious Annette demanded his murder.)

She could skip today’s proposed “training” with Duncan, but that’s useless when he knows where she lives and can quite literally kill her for refusing his demand, so she slips on a pair of black workout leggings and a purple-and-white patterned sports bra.Throwing a sweatshirt on, (Y/N) quickly grabs a water bottle and her phone before rushing out the door so as not to be late. Although she doesn’t know much about Duncan’s personality, she assumes that he hates people who are late.

The man in question is waiting inside the doors of the high-end training gym when (Y/N) enters, slightly out of breath from nearly running to make it in time. A small smile starts to spread across his face as he appraises her outfit, and (Y/N) self-consciously crosses her arms over her chest.

“Sorry that my clothes aren’t right off the runway like yours,” (Y/N) says as she gestures to Duncan’s figure. While he’s wearing workout clothes as well, his joggers and zip-up hoodie carry an air of wealth with them.

“They’ll do.” (Y/N) huffs as Duncan spins on his heel, repeating the same procedure as the last time they were here in order to get through the private door. 

There’s training mats set up in the open area next to the shooting range, and Duncan waits until (Y/N) places her stuff against the wall before walking to a bench and grabbing a roll of athletic tape. “We’re not doing shooting training today?” (Y/N) asks.

“No, I feel like you have a pretty good grip on shooting. Today I’m going to teach you how to fight, as that will most likely be what will happen if you do get into an altercation while under my orders.”

“When am I not going to be under your orders?” She rolls her eyes as she pretends not to watch Duncan take off his hoodie and reveal his strong, muscular arms. (Y/N) realizes that she’s never seen Duncan in shirts that didn’t have long sleeves, the monochromatic tattoos that decorate his skin coming as a bit of a shock.

“Once I decide that there’s enough to implicate you in crimes as well, if you were to ever run to the police.” She scoffs as he holds out his hand. “Give me your hand.”

She shouldn’t talk back, she knows, but she’s feeling defiant after hearing just how Duncan plans to keep her quiet. “Why?”

“This tape isn’t for me.” Giving her hand over, (Y/N) watches as Duncan swiftly wraps her wrist, checking the support of the tape on the joint before repeating the process on her other wrist. “This will help make sure you don’t injure anything. While the main goal today is to make sure you know how to take down an opponent, I also want to know that you know how to effectively punch somebody.”

Duncan lets go of her hands, and (Y/N) takes off her own sweatshirt before joining him in the center of the training mat. He’s conspicuously not looking at her chest, and (Y/N) bites back a laugh at the polite behavior of the crime lord before her. “Hold your hand out in a fist,” Duncan commands.

His eyes are narrowed in calculation as he studies her fist, adjusting her thumb so it’s on top of the space between the first and second knuckles of her index and middle fingers. He’s a good teacher, and he explains his reasoning as he makes adjustments, “you never want to have your thumb tucked inside your fist. You’re almost guaranteed to break your thumb that way.”

“Thumb on the outside, got it.”

Duncan steps back, holding his arm up with his palm facing (Y/N). “Punch my hand.”

“What?” (Y/N) looks at him warily. “I’m not going to punch you! What if I hurt you?”

“I promise you won’t hurt me,” Duncan says with a laugh. “Now punch.”

(Y/N) squares her shoulders, rearing her arm back before punching Duncan’s hand as hard as she can. He nods, and she punches once more, this time with her other fist. “I’m impressed,” Duncan says, “you punch really well.”

“I’ve taken a couple of self-defense classes in the past. They didn’t teach punching, but they did teach how to throw your weight into your hits.” Duncan’s eyes flash with a hint of pride, and (Y/N)’s chest uncharacteristically clenches at the thought of making him proud.

“Great, then we don’t need to work too much on that. Unwrap your wrists and we’ll practice some sparring.”

It seems like a good part of her life lately is following Duncan’s directions, but (Y/N) complies anyways. Duncan’s joggers look like they were tailored specifically for him, his black tank top showcasing the tattoos (Y/N) had found herself staring at earlier. This time, Duncan does notice. “Do you like my tattoos?” Duncan asks with a smirk.

“I just--you don’t seem like the type of person to have tattoos,” (Y/N) stutters.

He quirks an eyebrow in amusement. “I’m a mob boss.”

“Still don’t seem like you’d have tattoos,” she mutters before placing her hands on her hips. “What’s the goal here?”

“The goal is to take me down. When you’ve had me on my back for five seconds, today’s training will be over. However, there will be no dirty moves, got it?”

“But kicking someone in the balls is okay if I’m fighting an attacker, right?”

“Yes, but not in a practice scenario.” Duncan starts to slowly circle (Y/N), watching as her spine stiffens under his gaze. “I suppose I should warn you that I will not make this easy for you. You will be fighting to win, not fighting to learn.”

(Y/N) nods, turning to stop Duncan from pacing around her. He takes two steps back, standing in a defensive stance as (Y/N) attempts to get a feel for how to spar. She snaps her arm towards Duncan suddenly, in an attempt to catch him by surprise, but the man simply blocks it with a quick dodge.

The punch leaves (Y/N) defenseless, and Duncan lunges forward to shove her. He would never actually punch her; he’s been trained in combat since he was 10, and she learned to throw a proper punch 10 minutes ago. It would be unfair of him to swing at her, so Duncan settles for pushing her instead.

(Y/N) attempts to regain her footing, but Duncan’s too quick. His arm wraps around her neck in a chokehold, and (Y/N) gasps for air as she tries to wriggle out of his grasp. Avoiding panicking, (Y/N) thinks desperately to the aforementioned self-defense classes, trying to remember any of the acronyms the instructor swore would save the class’s lives one day.

Rearing her arm towards her body, (Y/N) swings her elbow back as hard as she can to elbow Duncan in the stomach. He releases her with a pained groan, obviously not expecting that move, and she turns around and kicks at his leg. 

“Fuck you,” Duncan gasps out, stumbling backwards but refusing to fall.

“Fuck you!” (Y/N) retorts. “You tried to choke me out!”

“And I warned you beforehand what you were getting into.” The two move warily, neither person wanting to make the next move. (Y/N)’s eyes crackle with anger, and Duncan grins wildly at the fierce expression she wears.

He swings once again, (Y/N) dodging before punching him in the chest. Duncan seizes the opportunity to sweep her leg with a well-placed kick, and (Y/N) goes falling to the mat with a thud. She inhales heavily, trying to get her lungs to work again after having the air knocked out of them. (Y/N)’s barely able to scramble backwards before Duncan is on top of her, his legs straddling her waist as his hands pin her wrists above her head.

Chests heaving, both Duncan and (Y/N) glare at each other as he waits for her to give in, but she refuses to admit defeat. She becomes acutely aware of the fact that Duncan is pinning her down to the mat with his weight, his strong hips against hers making movement impossible. It’s borderline-indecent, and (Y/N) chides herself for finding being held to the ground any shade of arousing. Although she can’t tell if she wants to kick him or kiss him right now, she knows that Duncan feels the same when he glances from her eyes to her lips, and back again.

“Can you get off of me?” The end of (Y/N)’s sentence is muffled as Duncan presses his lips to hers.

The shock of being kissed by the man who just defeated her at sparring quickly wears off as (Y/N) eagerly reciprocates the action, feverishly kissing him back. Her hands flex in Duncan’s grasp, desperate to grab onto any part of him as a way to ground herself. Duncan refuses to acquiesce, so she brings one leg up to the back of his knee and applies as much weight to the vulnerable area as she can.

“Ah!” Duncan groans, the buckling of his knee giving (Y/N) the opportunity to flip them over. Now it’s she who has the upper hand, grinding her hips down harshly on him as she kisses him once more. Duncan licks at her bottom lip, attempting to gain access to (Y/N)’s mouth and getting frustrated when she refuses to let him slip his tongue into her mouth. He’s done playing nice, and nips at (Y/N)’s bottom lip hard enough to draw blood. He moans when the copper taste of blood hits his tongue, (Y/N) pulling away and panting harshly.

“You fucking asshole, that  _ hurt _ !” Duncan just chuckles, flipping them over once again and roughly yanking her leggings and underwear down her legs. (Y/N) lets out a surprised moan when Duncan’s finger runs over her clit, collecting some of her burgeoning arousal and using it to slide effortlessly into her cunt.

(Y/N) is not the type of person to engage in casual sex with a person she hardly knows. She’s not even sure she’s had an actual one night stand before; the couple times that she had, it’s been with somebody she knew fairly well. So to be under the most dangerous man she’s ever met, his fingers buried inside her as he works her open, is certainly unlike her. It would, however, be impossible to deny that she’s not thoroughly enjoying this endeavor.

One hand grabs at Duncan’s bicep, and (Y/N) briefly admires the elegant script inked into his skin. Her other hand goes to grab at his sizable bulge, gripping onto his erection as roughly as he’s currently fingering her. Duncan lets out a choked groan at the sensation that’s both painful and pleasurable. Once he’s decided that neither party can handle the tension any longer, he withdraws his fingers from her cunt and pulls down his pants.

After (Y/N) gives his shaft a couple of quick strokes, Duncan lines himself up with her entrance and thrusts into (Y/N)’s tight walls. Matching moans ring out through the training room as Duncan begins to set a quick and deep rhythm. (Y/N)’s hips snap upwards, meeting Duncan’s as the two thrust in tandem. Every other sound, feeling, or experience fades away as Duncan continually bottoms out in (Y/N)’s cunt, his balls slapping against her ass. Her head lolls back against the ground, giving her the perfect chance to admire Duncan’s lustful expression and how his hair falls into his face with each sharp roll of his hips.

(Y/N)’s head begins to spin as Duncan’s rhythm begins to stutter upon nearing his orgasm, and she bites down on the juncture of his neck and shoulder in an attempt to muffle a scream as she cums unexpectedly. He cries out at the sharp pressure of her bite and the fluttering of her walls, speeding up his thrusts before pulling out and tapping at (Y/N)’s bottom lip with the swollen head of his cock. 

She turns her head towards him, eyes glazed with lust as she opens her mouth. Duncan only needs to thrust into his fist a few times before he cums in (Y/N)’s mouth with a deep groan. Her lips are painted white with his seed, and he nearly cums again when she licks it all up before swallowing with a content hum. Duncan collapses next to (Y/N), whose bones feel as if they’re made of Jell-o. As they both come down from their highs, (Y/N) has only one thought on her mind: What the hell did they just do?


	4. Hit and Run

**Summary for the Chapter:**

> The fallout of an unexpected tryst, and the reader's first official foray into the criminal underworld.

**Notes for the Chapter:**

> Don't really have any notes for this one. Thanks for not getting mad at the breaks between posting.

The training gym remains silent as (Y/N) and Duncan feel the weight of what they’ve just done. Duncan has a content grin on his face as he stands, fixing himself until he looks like he hadn’t even been training, let alone fucking the woman who he’s blackmailing. The look of disgust on (Y/N)’s face makes him stifle a laugh as he holds out a hand for her to take. Instead, she just stares at him, slowly making herself look presentable without Duncan’s help.

“The look on your face directly contradicts the beautiful sounds you were making earlier,” Duncan teases.

(Y/N) can feel her face heating up as she stands, pushing Duncan to the side. “What we did was a mistake,” she says seriously.

“Really? Because I quite enjoyed it, and I think you did too.”

“Duncan, that can’t happen again.”

The smile falls off of his face, and he scowls. “And why is that?”

“Because I try not to make a habit of having sex with people that I can’t stand!”

“Aw, you can’t stand me?” Duncan sneers. “Is that why you were so eager for me to fuck your little cunt?”

“You say that like you’re not the one who kissed me first.” 

(Y/N) feels a sense of self-satisfaction when she sees how Duncan’s jaw clenches from her verbal barb. Enough of a silence commences that (Y/N) thinks she’s free to go, turning to leave and finally be free of the specter that is Duncan Shepherd. Duncan decides otherwise, grabbing her upper arm roughly and spinning her back around.

“Tomorrow night, you’re getting indoctrinated into my world. I have an arms sale that I’m overseeing at 10, and you’re going to be there with me.”

“Will I be free of my burden, then?” The second question goes unsaid, but it hangs in the air like a cloud:  _ will I be free of you? _

“That’s for me to decide,” Duncan spits, letting go of (Y/N)’s arm before she can shake herself out of his grasp. 

“Fuck you, Duncan.” (Y/N) grabs her belongings from where they were thrown on the floor before nearly running for the door.

Duncan manages to get one last jab in before the door swings shut behind you, shouting “you already did!”

(Y/N) groans angrily once she’s outside, the cool air doing little to calm her down. The sun’s just beginning to dip below the horizon, and she pulls her hands into the sleeves of her sweatshirt to keep warm while she walks. Her mind churns with all of the possible ways she could’ve verbally wounded him besides just saying “fuck you.” He’s so infuriating, so confounding, so--she’s yanked out of her thoughts (thankfully, since her thoughts were beginning to drift towards the sexual encounter she had just found herself in) by her phone ringing in her sweatshirt pocket.

Assuming that it’s Duncan calling to threaten her, she doesn’t even glance at the screen before answering with a harsh “ _ what _ !”

“Whoa, was not expecting that from you.”

Her shoulders relax when she hears the honeyed voice on the other end. “Sorry Madison, I thought you were someone else.”

Madison Montgomery is not the type of person (Y/N) thought she would ever be friends with. A former child actress with enough stories of rehab stints to rival her IMDb filmography, their paths are not two that would normally ever cross. Madison’s “friend,” Zoe (no matter how many times the two insist they’re just friends, (Y/N) sees the longing glances and the soft touches the pair exchange when they believe she’s not looking), was one of (Y/N)’s first friends when she moved to D.C. After becoming close with the political science student following a few school events both were required to be at, befriending Madison came naturally.

“By the sound of your voice when you answered, I’m assuming you’re glad it’s me instead of whoever else you thought it might be.”

“I’m definitely glad to be hearing from you.” It’s not a lie; Madison has been distant lately, and it was starting to make (Y/N) worry that she had done something wrong. “You went off the grid for a bit.”

“I was in negotiations for a new project, and it was taking up most of my freetime.”

“Did you get it?”

“Hopefully. They said that I’ll hear back soon. Anyways, I’m in D.C. for a few days and was wondering if you could find time in your busy schedule to hang out with me and Zoe who, might I add, has already said she could,” Madison says like she isn’t solely in the city to see Zoe.

“Absolutely! Just let me know what dates and times work for you and I’ll work something out.”

“Tomorrow night? We could have a wine night at Zoe’s after she gets done with work at around 8.”

The initial excitement (Y/N) feels at the plans with her friends fades away when she realizes she has other obligations tomorrow night. “Shit, I can’t. Maybe the next day?”

“Do you have a  _ date _ , (Y/N)?”

She scoffs. “I wish. I have to go to this boring study group for class.”

“Skip it.”

“I can’t, it’s for a class I’m already struggling enough in.” Fuck, she really hates having to lie to people she cares about.

“Boo, why do you have to care about your grades and your future career?” Madison sighs. “Alright, we’ll do something when you don’t have to study.”

“I’m sorry, Mads.”

“Hmm, you should be.” She doesn’t mean it, but it still stings a bit. “I’ll see you on Wednesday, then.”

“See you Wednesday.” Madison hangs up the phone before (Y/N) even finishes speaking; if it were anybody else doing that, she would think they were mad at her, but that’s just typical Madison behavior. 

Ducking back into the throng of people walking to and from their destinations, (Y/N) feels a pit of dread in her stomach as the knowledge of tomorrow begins to set in. Not only will she be seeing the man who she fucked and then proceeded to get into a fight with, but she’ll also be observing an extremely illegal arms deal taking place between mafia groups. She can only hope that she’ll make it out of tomorrow’s events unscathed, both physically and emotionally.

* * *

Duncan picks (Y/N) up outside of her apartment at precisely 9:00 p.m., citing a need to be early to the deal in some underhanded way to assert his family’s dominance. (Y/N) tries not to ogle at the car she’s currently riding, but that’s a task she’s failed at since the moment she saw the sleek black exterior parked on the side of the street. Duncan, of course, notices how desperately she tries to look unaffected by riding in a car that costs triple her college education.

“You look like you’re scared merely breathing will ruin the car,” Duncan teases, the first words either of them have said all night. 

“I kind of am. This is the nicest car that I’ve ever seen in my life.”

“Well, thank you. It’s an--”

“Aston Martin One-77, I know.” (Y/N) ducks her head in embarrassment when Duncan looks at her with wide eyes, assuming she shouldn’t have interrupted him. “I’m sorry, I know that was rude, but I’ve always really liked cars and while I don’t know a lot about fixing them or their engines or such, I love seeing a car and being able to name the make and model.”

“Don’t apologize, you didn’t do anything wrong. I just wasn’t aware that you liked cars.” He shoots her a sly glance, subtly revving the car to watch how her eyes light up. “If I had known, I would have picked you up in one of my cars a whole lot sooner.”

“Wait, you have more like this?”

“Of course. You’re not the only one who has an interest in cars.”

She’s thoroughly impressed now, a fact Duncan would know even if he wasn’t able to read people’s emotions like they’re the summary on the dustjacket of a book. He had been worried that she was either going to blow up about what had happened yesterday or completely ignore him, so this was a welcome surprise. As long as she doesn’t feel like talking about the events of the previous day, Duncan certainly won’t bring it up.

The location of this covert sale is, much like every other mafia-based experience, disguised behind a plain exterior. This time, it’s a small grocery store just over the Potomac that serves as the facade for illicit activities. Duncan parks the car in a side street so as not to arouse suspicion, turning the silent engine off before handing (Y/N) a gun.

“Don’t you have bodyguards to keep you from dying?”

“Yes, but...things can tend to go sideways during these types of events. It’s already a liability bringing you along, and since you know how to handle yourself around a gun now, it does no harm to be over prepared.”

(Y/N) eyes it warily, taking the weapon and checking the safety before tucking it in the waistband of her jeans. Duncan waits for (Y/N) to get out of the car before leading her up the stairs and through a loading dock. Even if she wasn’t too scared to go to the cops and she tried to put the Shepherds in jail, she wouldn’t be able to lead them to the location of the deal in this maze of a basement.

There’s already a small crowd in the room that they end up in, and (Y/N) holds back a shudder when she sees Langdon lurking in the corner. It’s obvious that a 10:00 meeting means 9:30 for syndicated crime, and Duncan’s a fan of being fashionably late.

“Mr. Shepherd,” the assumed leader, a tall raven-haired man with a Scottish accent, greets. “Have a seat.”

“I think I’ll remain standing, thank you, Mr. McCown.”

The man just barely scowls before turning his eyes on (Y/N). “Who’s the girl? You said no backup.”

“She’s hardly backup,” Duncan chuckles, a statement that (Y/N) takes minor offense to. “We agreed on one man each. I have Langdon, and you have Collum. (Y/N), here, is simply collateral damage.”

“Hmph.” McCown doesn’t look too pleased, but relents. “Are we gonna do business, then, or not?”

Duncan motions for Langdon with his left hand, who carries two large duffel bags to the table. Unzipping them, he reveals a variety of automatic weapons. McCown leans over the table to study the weapons, doing a mental count before reaching for the bags.

“Not so fast.” Langdon snatches the guns away from McCown upon Duncan’s word. “The money?”

Pulling open his suit jacket, the opposing crime boss sets stacks of hundred dollar bills on the table. Duncan appraises each stack quickly, thumbing through the paper with a learned precision. Each man watches the other as they grab their respective earnings, neither willing to be the loser in this staring contest. 

“You know, I couldn’t help but to notice you were a thousand short of the agreed-upon total,” Duncan says coolly.

“It’s all there, I just saw you count it!”

“The tax? (Y/N)’s eyes flit between the men, Duncan’s jaw tightening in annoyance. “This is not your first time doing business with us, Frasier, surely you must know that there is a fee to bring your men into our territory.”

McCown smiles thinly, reluctantly pulling another wad of cash from his pocket. Duncan smugly takes it, and it’s when he’s counting the cash that everything goes awry.

(Y/N) doesn’t see anything out of the ordinary. The Scottish leader is zipping up the weapons bags and D.C.’s most notorious is tucking the money into his own jacket. She’s not sure what Langdon detects: a tic on someone’s face, the flinch of a hand, or even just the way a person breathes. Within a second, he’s got a handgun drawn and pointed at McCown’s right hand man, firing before the other man can even release the safety on his own gun.

Duncan ducks, pulling (Y/N) down under him as gunfire is exchanged. Her heart hammers in her chest, ears ringing from the harsh sounds above her as the shots start to taper off. She doesn’t even have time to process what just happened before Langdon’s yelling at them to go, Duncan hauling her up and throwing a duffel bag at her before dragging her out of the room. The clouds of gun smoke make it impossible to see who, or what, is damaged, and her eyes and lungs sting from the acrid scent as she runs up the stairs with Duncan.

Flinging herself into the car, she doesn’t even have time to put a seatbelt on before Duncan’s peeling out of the alley with the tires squealing. Instead of being frightened, Duncan actually looks excited as he checks behind his shoulder to make sure he’s not being followed. (Y/N), on the other hand, sits next to him in utter bewilderment.

“What the  _ fuck _ was that?” (Y/N) exclaims, tossing the bag down at her feet when she realizes she’s still holding assault weapons.

“ _ That _ was an attempted underhanded deal.” He clarifies upon her bemused shrug. “Frasier McCown and his gang thought that they would shoot me before taking the weapons and their money.”

“They were trying to kill you?”

“Probably not. They were most likely just trying to make sure I would go down before worrying about the repercussions later.”

“Langdon killed them, then?”

“I don’t know for sure, but he’s absolutely deadly with a gun. You’ve seen how skillfully he kills people.”

(Y/N) nods, remembering how the shot that killed the blue-haired Malakai seemed to come from nowhere. Looking out the window, the freeway passes by in a blur as Duncan drives towards downtown D.C. He’s trying to lose them, she realizes, on the off-chance that they are being followed.

Swinging into an empty parking lot off of 14th Street, the car lurches forward as Duncan abruptly parks. His hand gently brushes (Y/N)’s cheek, and she nearly bites his finger off until she feels the sting of a fresh cut on her face.

“You’re hurt,” Duncan notes with a frown.

“Oh, I probably just got scraped when we went to the ground. It’s fine, I think I’ll live.”

Duncan scoffs, rolling his eyes as he examines her to make sure there are no other wounds. Besides the battle wound on her cheek, she seems okay.

“What--” (Y/N) starts, clearing her throat, “are you hurt?”

“No,” he answers quickly.

“Are you sure?”

“(Y/N), you don’t need to worry about me. I’ve been in these situations before, and I have no doubt that I’ll be in situations like that again. This was your first time being caught in a firefight, and you’re shaking, so I just want to make sure you’re not in shock.”

“I’m not…” (Y/N)’s about to argue until she looks down and sees that her hands are shaking. “Oh.”

“Yeah,  _ ‘oh,’ _ ” Duncan mocks. “You’re sure you’re okay?”

“I’m good.” She starts to lightly giggle before breaking out into full-on laughter, making Duncan worry that she actually is going into shock. “No, seriously! I’m fine, I just--that was kind of cool.”

Duncan looks at her incredulously. “You thought that was  _ cool _ ?”

“Yes! It felt like I was in a James Bond movie.”

Despite his attempts to be serious, Duncan finds himself smiling at her exuberant laughter. “Well, I’m glad you thought that was fun. Hopefully we won’t be doing that again anytime soon.”

Later, (Y/N) will swear it’s the adrenaline rush that makes her act so foolishly. But with the silence in the car, and the way that Duncan’s smiling at her, it feels like she’ll spontaneously combust if she doesn’t kiss him immediately. Before she can remind herself why this is a bad idea, she leans in and presses her lips to his.

Duncan, thankfully, doesn’t immediately push her off and question her sanity. His lips are just as soft as they were yesterday, one hand going to grip the back of her neck while the other brushes against her cheek. (Y/N)’s hands find purchase in his now-messy hair, fingers threading through the strands as Duncan licks at her bottom lip. This time there’s no resistance from (Y/N), her mouth opening to allow Duncan’s tongue entrance while they grab onto each other like they’ll be torn away otherwise.

Relishing in the breathy moans (Y/N)’s beginning to let out, Duncan reluctantly pulls himself away from her lips in order to trail kisses down her neck. Laving his tongue against her thrumming pulse, Duncan grins when (Y/N) whines as he blows air over the wet patch, leaving goosebumps in its wake. He begins to suck a bruise just below the spot he just marked, nipping just enough to make (Y/N) yelp before surging back up to her lips.

(Y/N)’s head is spinning, the mix of adrenaline and lust making her almost dizzy. When Duncan finally releases her from his grasp after  <strike> minutes? hours? </strike> an undetermined amount of time, she lets out a whine that sounds almost pathetic. Duncan wipes his mouth on the back of his hand, lips swollen from the extended amounts of pressure as he suddenly and inexplicably starts to drive. (Y/N)’s about to question why he stopped when, like a flash of lightning, the situation hits her with striking clarity. Kissing Duncan Shepherd in an abandoned parking lot like a couple of horny teenagers directly goes against everything she told him after their “training” yesterday.

From the driver’s seat, Duncan smirks when she faces the window with her arms crossed over her chest, obviously realizing her little slip-up. “Another mistake?” He can’t help himself from taunting her, especially not when she looks so upset with herself.

(Y/N) sneers. “Shut up.” Still, it doesn’t go unnoticed by Duncan how she subtly clenches her thighs together in search of relief, giving him a self-righteous sense of satisfaction.


	5. The Less You Know, the Better

**Summary for the Chapter:**

> (Y/N)’s acutely aware of the potential ramifications of slipping up about what’s kept her so busy lately while out with friends. Welcome to chapter 5 of Memento Mori.

**Notes for the Chapter:**

> Yes, I know this is terrible. Yes, I know it’s short. Listen, sometimes you have a point A and a point B with no idea how to get from each. I tried. Feedback is always appreciated, and if you somehow liked this, leave a kudos or comment.

Duncan was out of the country on “business.” Whether that was actual legal business or more clandestine dealings, (Y/N) wasn’t sure. He had been deliberately vague on where he was going and what he was doing, although (Y/N) suspected that it was due less to a need for secrecy and more because Duncan enjoys having information that others don’t. While it’s certainly nice to not always be dreading her phone going off for fear that it’s Duncan ripping her out of her daily schedule, she feels a little lost on what to do. Her life lately has almost solely revolved around making sure not to piss off the mob boss who could very easily procure some “evidence” implicating her in crimes and put her away in prison for a long time. It’s an odd freedom, but she’s acutely aware that this does not mean that she’s not being watched.

Her head still feels cloudy, last night’s events converging in her memory like a storm system. She wasn’t able to sleep, echoes of gunshots and ghosts of soft lips on soft lips keeping her from fully finding unconsciousness. For a brief moment this morning, she had considered cancelling today and staying under the covers where nothing bad could get her. However, she knew that Madison would come marching into her apartment and drag her out of bed if necessary. Coming face-to-face with Madison’s rage is an outcome that she would rather not deal with the day after being caught in a gunfight, and so (Y/N) begrudgingly gets dressed, knowing that, no matter how bad today is, she’s not having to deal with Duncan Shepherd.

Right now, however, (Y/N)’s not sure what’s worse: accompanying the head of the Shepherd family to illicit weapons deals, or spending a day with Madison. She loves the blonde, really, but brunch (complete with mimosas, because “really (Y/N), it’s almost sacrilegious to not have a mimosa at brunch”) and shopping is dreadful enough that she considers ditching before remembering that she had made a promise, and promises are meant to be kept.

The only thing that makes this day out tolerable is the dance that Zoe and Madison do to hide the fact that they’re absolutely together. (Y/N)’s not sure if they think she’s too preoccupied to notice or if the pair just thinks they are that good at covering their tracks, but it’s enough entertainment to get through listening to Madison compare crudités and canapés. Madison will realize that she’s been staring at Zoe just long enough for people to get the  right wrong idea, or Zoe will find her fingers unconsciously drifting closer to Madison’s in an attempt to hold hands. Soon enough, Zoe or Madison will slip up enough where they’ll have to come clean, but until then, (Y/N)’s content to wait it out.

Like everything lately, being out with friends eventually leads (Y/N)’s train of thought to Duncan. She wonders if he has spies on her right now, her first real chance to betray him if she wanted. Maybe he’s not even out of the country; it’s entirely possible that he’s still lurking around D.C., hiding in the shadows and waiting for the right moment to finally watch her slip up and kill her. (Y/N) shudders at the thought, hoping that she truly is as insignificant to Duncan’s business as he always claims she is.

“Are you even listening to me?” (Y/N) jumps when Madison’s hand lands on her shoulder, the light of whatever shop they’re in (when did they leave brunch?) reflecting off of her pink-painted nails.

(Y/N) nods. “Yeah, absolutely. I was just giving you a chance to finish talking.”

“Really? Because I’ve been waiting twenty seconds for your response.”

Her face heats up. “I had to think over my response.”

Madison looks entirely unimpressed, but Zoe appears from the dressing room before she can question (Y/N).

“I feel like this might be a little too dressy, but I’m not sure.” The brunette nervously smoothes her hands over the fabric of the evening gown, eagerly awaiting feedback.

“What’s this for?” (Y/N) asks.

“There’s this charity event I might have to go to, so I figured I’d be prepared.”

“It’s nice,” Madison says, eyes sweeping over Zoe’s lithe figure, “but what about the blue one I grabbed for you on the way in? The off-the-shoulder one with the full skirt?”

Zoe bites her lip, averting her gaze to a wall of shoes. “The price is...way out of my budget.”

Madison stands quickly and grabs Zoe’s arm. Although she tries to speak quietly, (Y/N) can hear every word. “You know that I’ll gladly pay for anything you could ever want.”

“I can’t let you do that--”

“Yes, you can. I want to do it, I don’t have to. Besides, I can probably get reimbursed if it’s that much of an issue to you, since this will be for official business.”

(Y/N) wants to ask what ‘official business’ means, but the disagreement is settled before she can. Zoe turns around and goes back into the dressing room as Madison sits down next to (Y/N), oozing satisfaction out of every pore.

“What was that about?” (Y/N) asks with a chuckle.

“Zoe’s too thrifty to ever treat herself, so I offered to buy her a dress for this event.” Although (Y/N) gives Madison a look that says she is not buying it, Madison refuses to amend her statement.

“Did you get the part that you were up for?” (Y/N) chooses to drop the previous subject for now.

“The what?”

She frowns. “You told me on Monday that the reason you were never answering your phone is because you were in negotiations for a project.”

“Oh yeah. The project fell through, it was a little too avant-garde for my taste.”

“You haven’t had acting work for over a year now, and yet you turned down a role?” (Y/N) regards Madison with suspicion. Madison’s never been shy about taking almost any role offered to her, which is why this decision is so odd. 

“I’ve been busy with other pursuits lately.”

“Pursuits that make you enough money that you’re able to purchase Zoe, what I’m assuming to be a high three-figure dress?”

Madison’s mouth tightens until her plum lips are little more than a thin line. “If I told you what I was doing, I’d have to kill you.”

(Y/N) lets out a sharp laugh of surprise. “Trust me, I’ve heard a lot of dangerous information lately.”

“What, is your little study group looking into unsolved murders or something?” To any outsider, the harsh volley of questioning would make them worry that the two women were about to start attacking each other. Verbal barbs, however, are an integral part of their friendship.

“I wish. That would make things a lot easier on me.”

Madison’s eyes soften, and she moves a seat closer to (Y/N). “Hey, is everything okay with you? On the phone the other day, you sounded really angry and frazzled, and today you’re spacing out like you’re somewhere else. Is something going on?”

She wants to tell Madison so badly, and, for a moment, she considers the ramifications of what would happen if she did. Surely Madison would be able to keep a secret if (Y/N) asked, and it would be so relieving for just one person to know the shit she’s having to go through right now. On the other hand, Madison could freak out and tell the cops that her friend is being blackmailed, or clandestinely record information about the Shepherds’ illegal activities and get them locked up, which would most likely get (Y/N) killed. A third option would be word getting back to Duncan that (Y/N) had told someone, which means two out of the three potential avenues involve being killed. Considering her odds, (Y/N)’s resigned to having to keep this secret a secret.

(Y/N) settles for a half-truth. “There’s just...a lot of changes happening really fast, and I’m not sure if all of them are positive.”

“Like you and Zoe graduating in a few months?”

(Y/N) blinks slowly, realizing that she had completely forgotten that their impending graduation was even an event on the calendar. “One of many things that has me preoccupied.”

“Look, obviously I don’t know too much about education considering I was pulled out of school in fifth grade to star in the film version of ‘Goosebumps’ and didn’t get my GED until I was almost 20. If there’s anybody who’s absolutely prepared for life after graduation, it’s you and Zoe. Plus, if you decide that you’re not ready for a professional job, there’s always graduate school, right?”

“Yeah, you’re right.”

“Of course I am, I’m always right.” Madison flips her hair over her shoulder in a move that reminds everybody in the room that she is, first and foremost, an actress. “I feel like there’s something else though.”

“Right again.” (Y/N)’s racking her brain for a suitable lie when Zoe exits the dressing room, a pleased flush on her face at the noises of approval her friends make. 

“You guys really like it?” Zoe asks shyly.

Madison nods. “It’s perfect, Zo!”

“This is an event that the poli sci department is hosting?” (Y/N) speaks, not recalling the campus putting out any sort of an announcement for an event such as this.

Zoe shakes her head. “No, it’s something that my extended family participates in, and they want me to go with this year.”

“Get the dress. Seriously, you’ll be the most stunning one at this party.”

Madison can see the hesitation on Zoe’s face, and she jumps in. “Don’t even think about the price, okay? Go and get changed and then wait outside, I’ll handle paying.”

At Madison’s urging, Zoe retreats into the dressing room. 

“So what else is on your mind?”

(Y/N) huffs, standing up and beginning to gather their various personal belongings. “It’s really complicated.”

“I thrive in complexity. Try me.”

“I got…” forced to be a mob leader’s lackey? “roped into something that people would never expect me to be a part of.”

“Like a BDSM group?”

If only it were that simple. “Uh, no. Anyways, I didn’t realize what was going on beforehand, and now I’m sort of stuck for the time being.”

“Sounds exciting. Are you a spy for the CIA?”

“That’d be cool, but no.”

“Do you want to quit whatever it is that you’re involved in? I’m getting conflicting emotions from you regarding this.”

(Y/N) pauses. It seems like the obvious answer would be that of course she wants to quit. She’s basically being blackmailed with the threat of either death or prison if she doesn’t comply to whatever stupid demands Duncan Shepherd has for her. At the same time, her life has never been more crazy and exciting than it has the past couple of weeks. The danger, the mystery that comes along with interacting with organized crime is a shot of adrenaline straight to the bloodstream. It’s a complicated answer, but it’s one that (Y/N) doesn’t have to come up with right away when she’s saved by Zoe coming out of the dressing room. 

“Alright, let’s get out of here before the perfume and pop music gives me a migraine.”

Madison sends (Y/N) to wait outside with Zoe while she pays, coming out of the shop with a paper bag that looks far bigger than what is needed for a single dress. Zoe shares a look with (Y/N), both knowing that Madison bought at least two sets of jewelry to go along with the dress. It’s already almost 1 p.m., at which Zoe and Madison both have their own respective engagements (although (Y/N) has a suspicion they just want to go on a date), so they bid goodbye with a hug and a promise to get together at least once more before Madison leaves town. (Y/N) doesn’t miss the pair walking the same direction, or the way their hands meet and grasp onto each other. Subtle is not a word that could be used to describe their relationship.

(Y/N) smiles as she walks the opposite way, her friends’ hidden romantic interactions causing butterflies to fill up her chest cavity. It’s a perfect day today, the temperature just warm enough that a light sweater is all that’s necessary to be outside. She’s considering stopping to get a pastry from the little bakery just down the street from her apartment, potentially even getting her backpack and doing some homework outside of her apartment. It’s a pleasant thought, and it has her mind so preoccupied that she doesn’t notice the shadow in the alley until they’ve snatched her and dragged her away from the street.

The rough brick of the side of a building scrapes against (Y/N)’s back, but that’s the least of her worries once she feels cool steel pressing below her ribcage. Regaining her bearings, her breath catches in her throat when she meets the cold, almost unhinged blue eyes that could only belong to one man.

“Langdon,” (Y/N) gasps, “what--what are you doing?”

“Well, I was simply enjoying my day when, to my surprise, I see you. Naturally, I thought I’d say hello and ask what the hell you were doing meeting with two of the top members of the Coven?” He jabs the steel further into her skin, and (Y/N) can feel the blood draining from her face when she sees the gun in Langdon’s hand. “ _ Don’t lie _ .”

(Y/N) whimpers, closing her eyes in fear. “I--what’s the Coven?”


	6. What, Like It's Hard?

**Summary for the Chapter:**

> Before Duncan makes it back to properly interrogate, (Y/N) deals with an odd dinner guest.

**Notes for the Chapter:**

> Hey hi hello, it's time for another chapter of Memento Mori. As always, kudos and comments are appreciated if you enjoyed, and if you didn't, send me anon hate on Tumblr @7-wonders and we can set up a time for a cage match to the death.

As it turns out, Duncan actually  _ was _ out of the country on business. By virtue of being so far away, (Y/N) had been placed on house arrest by Langdon until Duncan could make it back stateside to properly interrogate (Y/N). Interrogate her for what, she wasn’t sure. Langdon refused to answer any of her numerous questions about what “the Coven” was, and why her friends were involved with it. Although he knew that her bewilderment towards his pulling a gun on her in the alley was not faked, he still treated her as if she were the enemy.

Langdon’s also annoyingly good at his job. (Y/N) never sees him, yet she knows he has eyes on her at all times since he’s managed to stop all three of her attempts to sneak out since he’s imprisoned her in her own home yesterday. While it’s a little creepy to know that someone’s always watching, Langdon easily blends into the background like some piece of furniture. Begrudgingly, (Y/N) has to admit that his presence in the house is weirdly comforting. After all, there’s nothing more dangerous in the world than Duncan’s right hand man. 

(Y/N)’s making dinner when an idea occurs to her. It could either be very good or very bad, but since she really has nothing to lose at this point, she might as well go for it. 

“Hey, Langdon?” (Y/N) asks after she’s finished cooking. There’s silence, which she expects, so she turns around after a moment to see him standing at the entryway to the kitchen. “I, uh--I’m guessing you haven’t left my place since you brought me here yesterday. Do you want something to eat?”

He looks perturbed as he leans against the wall. “I was seconds away from shooting you yesterday, yet you...want to feed me?”

(Y/N) shrugs. “Shit happens. You were just doing your job.”

The odd pair stares at each other awkwardly, neither one sure what move would be best to make. Briefly, Langdon wonders if (Y/N) has the wherewithal to actually attempt to poison him. However, she looks like she just genuinely wants to offer him some food, so he decides to take the risk.

“Well,” (Y/N) grabs a bowl and fills it with pasta, “I assume you know how to serve yourself, and since I’m not a waitress…”

She almost thinks that she hears Langdon snicker under his breath, but a second glance shows the same impassive face that he always has. She moves past him to allow him some space, sitting down on the couch and pulling out her phone. Thankfully, the assassin doesn’t sit down next to her, choosing to blend into one of his many hiding spots and eat his meal. 

The thing about Langdon being so good at his job is that it’s easy to forget that he’s around. “You’re a good cook,” his suave voice says from behind (Y/N), making her jump slightly. It’s an improvement from yesterday, when she opened up the front door with the intent of checking the mail and nearly screamed upon seeing Langdon on the other side, unaware that he had even left her home.

“Thanks, but it was just pasta. Anyone can throw some pasta into a pot of boiling water.”

“Even if it is something everyone can do, thank you for offering some to me.”

For the first time, (Y/N) smiles in Langdon’s presence. “Well, you’re welcome.”

Although Langdon doesn’t sit down on the couch, he does hover instead of just disappearing again.

“Is--is Langdon your first name, or your last name?”

His lips quirk into something that could resemble a smirk if he tried. “What do you think?”

“I think you have a boring first name, so you just go by your last name.”

He raises an eyebrow, and it seems like he might indulge her until the front door opens and Duncan Shepherd walks in. He looks harried, like he rushed here immediately after getting off the plane. It wouldn’t surprise (Y/N) if that were the case, but she really doesn’t understand why she continually gets treated like she’s the most dangerous woman in America right now. Really, the empty bowl on the coffee table is more dangerous than (Y/N) could ever be.

“You missed dinner,” (Y/N) calls, Duncan doing a double take when he realizes Langdon actually looks like he was relaxed. “Take your shoes off, I don’t want dirt all over my floors.”

“You’re...not dead yet?” Duncan asks, eyes continuing to dart back and forth between (Y/N) and Langdon.

“I don’t believe I’m dead. Were you hoping I would be?”

“I just assumed that you would annoy Langdon to the point where he would rather kill you than listen to you talk.” There’s the cocky Duncan that (Y/N)’s so familiar with. “I can take it from here, Langdon.”

Langdon nods, Duncan grabbing his arm and whispering a few words into the blond’s ear before letting go of him. Even after the door closes, Duncan remains silent. (Y/N) fidgets with anticipation; she has no reason to be nervous since she’s done nothing wrong, but she still worries there’s some sort of unspoken mafia rule that she broke.

“I know that you don’t know anything about the Coven.”

(Y/N) looks up at him in shock. “I don’t, but why do you believe me?”

“Langdon actually would have killed you if you did. He only entertains those who have information until he gets bored,” Duncan smirks at (Y/N)’s bewilderment.

“So, then what is the Coven?” (Y/N) asks, eager to change the subject from the myriad of ways in which Langdon could end her life.

“A threat to my family’s empire.” (Y/N) rolls her eyes and laughs, making Duncan scowl. “This isn’t a laughing matter!”

“This entire criminal world is a laughing matter.”

“You thought that I was terrifying? That  _ Langdon _ was? The things the Coven does to their enemies--tongues cut clean out of mouths and the people left still alive, extremities removed with surgical precision, tortured bodies that look like they’ve been drained of every pint of blood--would be enough to give you nightmares for weeks.”

“Okay, so the Coven isn’t good. Worse than you, if that was even possible. Why did Langdon think that I was involved with them?”

“Because you were out with two suspected members of the Coven.”

(Y/N) thinks back on the events leading up to Langdon snatching her back into an alley. “Wait, Madison and Zoe?”

“Madison Montgomery has been seen at Coven-backed establishments, as well as accompanying their leader to a number of events. We have reason to believe that she’s persuaded her girlfriend, Zoe Benson, to use her position within the federal government to the Coven’s advantage.”

She sighs, long and slow, trying to adjust to the idea that even her closest friends aren’t immune from organized crime. “What does this have to do with me, though?”

“Well, I figured I could use your relationship with both Madison and Zoe to help gather some information on what the Coven is doing.”

“No!” The word comes out before (Y/N) can realize she’s said it, but she doesn’t regret saying it.

A muscle twitches in Duncan’s jaw, his blue eyes blazing with anger. “What do you mean, ‘no?’”

“I’m pretty sure you know what that word means.” She stands and stalks to the other end of the living room, needing to get some space before she says something she’ll regret.

“Might I remind you that you are still indebted to me for sparing your life? I decide when you’ve repaid that little favor, and I decide what you do to repay that favor.” Duncan stands as well, keeping some distance in case she decides to try something.

“Kill me, then! I’m done catering to your whims, I’m done having to do illegal things for you, and I’m especially done with you. I don’t care what happens to me. Have me thrown in jail, torture me, make my death look like an accident, but I will not betray my friends’ trust just because I was at the wrong place, at the wrong time.”

Before she can even blink, Duncan’s large hand wraps around her throat as he slams her into the wall. The back of her head throbs, but the murderous gleam in Duncan’s eyes sends a cold shiver of fear down her spine. He’s cutting off her air supply, and though she attempts to claw his hand off of her neck, his other hand grabs both of her wrists and keeps them locked at her waist.

“Do you see how easily I could kill you? If I just tightened my hold,” he demonstrates what he means, making spots of black appear in (Y/N)’s eyesight, “or loosened it,” she gasps as his hand goes lax, sucking in just enough air to keep her from passing out. “I can decide whether you live or you die. I suggest you keep that in mind.”

“Do it then,” (Y/N) struggles to speak with Duncan’s hand nearly closing her windpipe. “Don’t be a coward; kill me if that’s what you want.”

Duncan glowers at her. “You’re fucking infuriating, do you know that? You’re the most stubborn woman I’ve ever met.”

Then, he leans forward to kiss her. His grip on her throat loosens as he becomes more invested in kissing her. (Y/N) could easily slip out of his hold now, but, truth be told, she doesn’t really want to.  _ Am I this fucked up that Duncan demonstrating how he can kill me turns me on? _ , (Y/N) thinks to herself as she kisses him back.  _ When did I start being into choking? _ She can’t deny that the whirlwind of emotions that she experiences when she’s with Duncan, often leading to some sort of sexual activity, gives her a thrill that she’s never felt before.

“Jump,” Duncan commands, tapping on (Y/N)’s thigh. She does as he asks of her, and continues to kiss up and down his neck while Duncan walks in the direction of her bedroom.

“Wow, you’re actually going to fuck me on a bed this time? What a gentleman,” (Y/N) quips sarcastically. 

Duncan drops her on the bed in response, barely giving her time to settle before he’s hovering over her again. “It’s a shame nobody’s ever punished you for your disrespect.”

“And you think that’s what you’re going to do? Punish me for my perceived disrespect?” She’s taunting him now, going on the offensive in this dangerous game that they’ve engaged in. Though (Y/N) verbally challenges him, she still removes her clothes with the same vigor as Duncan shows while removing his own outfit. 

“I get the feeling you would enjoy my punishments far too much.” Duncan bares his teeth in a sharp grin, causing anticipation and want to well in (Y/N)’s stomach.

He crawls towards her on the bed after getting rid of his pants, (Y/N) leaning back against the headboard as she wraps her arms around his neck. She knows she’s making yet another mistake, and that, if she had any sort of sanity remaining, she should send Duncan on his way with blue balls. But she’s not, and she’s prepared to reap the benefits of this sinfully-rewarding mistake.

Duncan kisses her once more, distracting her from her thoughts as he runs a hand down her bare abdomen and to her core. Once he’s decided that he can’t wait any longer, he lines himself up with her and thrusts in. Twin groans echo in the air of (Y/N)’s bedroom as Duncan immediately begins an unforgiving pace.

“And you thought I was going to make you become a call girl when our paths first crossed,” Duncan chuckles, reveling in (Y/N)’s whines and moans as he rails her into the mattress. “I would never let anyone else near this sweet little cunt that was made just for me.”

(Y/N) gasps at the eroticism of his declaration, allowing Duncan to wrap one of her legs around his waist so that he can angle himself. It works, with the head of his cock brushing up against the spot that takes her breath away and makes her dig her nails into his back.

“You’re mine, do you understand that? Nobody could know every part of you like I do.”

Laughing harshly, (Y/N) retaliates by raking her nails down his skin. “You don’t know me.”

“I know more about you than you think. Specifically,” his hand falls to her clit just as he speeds up, making stars explode in her eyes as she unravels, “I know just how to make you fall apart.”

The clenching of her walls around him combined with a look of rapture that could rival a Renaissance painting in terms of beauty has Duncan hurriedly pulling out, lest he spill himself inside of (Y/N). A couple thrusts into his hand result in release, his seed painting her abdomen. Boneless in a way that he hasn’t felt since he first became sexually active as a young man, Duncan collapses next to (Y/N) on the bed, having just enough strength to grab a couple of tissues and clean up his mess. 

Basking in a post-sex haze, (Y/N) is entirely unprepared for what Duncan says when he opens his mouth. “What’s the nicest dress that you own?”

Out of all the weird things that Duncan has said in the short time that he’s been in (Y/N)’s life, this has to be the weirdest. “Uh, I think I might still have my senior prom dress at my parents’ house. Why?”

“Since you’ll be attending the annual Presidential Honors’ Gala,” he wraps an arm around her shoulders and kisses (Y/N)’s forehead, an unexpectedly soft move that she just chalks up to the excess flow of dopamine, “as my plus one, of course.”

She sits up in the bed, holding the sheets to her chest to reserve some shred of dignity, as if Duncan didn’t just see every inch of her in the biblical sense. “You...want me to go to some gala with you?”

He nods, as if it’s the most obvious thing in the world. “Yes.”

“Why?”

“You’ll be a new face, which means that you won’t raise the suspicions of others in my world.”

(Y/N) sighs. “Great, so this is a mafia affair?”

“Officially, no. Unofficially, it’s become  _ the _ event for the Washington crime syndicates.”

“What would I be doing?”

“Besides being my entertainment on an otherwise boring night? You would help to gather some simple information from one of my biggest threats.”

“I’m not changing my mind about the Coven thing,” (Y/N) says tensely.

“I have more than one enemy, darling.” The pet name makes her nose wrinkle, but she remains silent. “So? What do you say?”

She doesn’t say anything. She does, however, nod just slight enough for Duncan to see. He grins satisfactorily, though (Y/N)’s expression does not match. Instead, she’s trying to figure out where the hell she’s going to find a dress elegant enough for a date with a mob boss.


	7. If You Want Peace, Prepare for War

**Summary for the Chapter:**

> Being conscripted to be Duncan’s undercover spy at a gala leads to (Y/N) becoming far more entangled in this dangerous world than she could have ever imagined.

**Notes for the Chapter:**

> Thank you guys for being so patient with me as I wrote this next chapter of Memento Mori! I sincerely hope you enjoy, and remember that kudos and comments make my world go round. Also, check me out on Tumblr @7-wonders for more!

Thankfully, (Y/N) doesn’t have to search through all of the greater-D.C. area in an attempt to find a dress for an event that she has no clue how to dress for. After a week of searching online every chance she got, she had almost considered ruining the tepid civility she and Langdon had reached by calling Madison and asking for her help on what to wear. Whether Duncan knew that (Y/N) was struggling or he just didn’t want her to embarrass him by showing up underdressed, he comes in at the midnight hour with a solution. A knock at (Y/N)’s apartment door the morning of the gala precedes a package sitting on her doorstep.

(Y/N) doesn’t open the large box until it’s sitting on the coffee table, suspicious about its contents. After all, it wouldn’t be too far-fetched to think that the repercussions of the gunfight she had unwittingly been a part of had followed her back home. However, since it doesn’t feel like it’s heavy enough to have a bomb inside, and anthrax is usually sent in envelopes, she feels safe opening the lid. There’s a note addressed to her on top of a pile of tissue paper, and she picks it up to read it.

“Assuming you won’t know what to wear tonight, here is something that will suit both your tastes and mine. If you do hate it, take solace in the fact that you’ll only have to wear it for one evening. Be ready by 8. Yours, Duncan.”

Although mildly perplexed by the ending to his letter (and feeling almost like Angelica in _Hamilton_ the longer she lingers on that one word), (Y/N) pushes that to the side to see what dress Duncan has procured for her. And what a dress it is. She gapes at the silky fabric under the tissue paper, a shiny black that feels like it’s satin. Pulling it out of the box, she sees that it is, in fact, satin. The dress is a V-neck with delicate spaghetti straps, a ballgown silhouette hiding a side slit that looks as though it will go up to her thigh. Checking the tag, (Y/N)’s not at all surprised that it’s her size. Instead of lingering on the question of who was going through her closet in order to find her size, she tries to staunch the sudden influx of nerves by doing anything to distract herself from the evening’s impending events.

Eventually, the evening does roll around. While (Y/N) doesn’t consider herself an expert on hair and makeup, she has to admit that she looks pretty good while appraising herself in the mirror. Her hair is naturally loose, yet styled to look like she put more effort into it. The deep red lipstick she chose perfectly compliments the black dress that she’s wearing, the V-neck showing off just the right amount of cleavage. (Y/N)’s just slipping on a pair of low black heels when Duncan knocks on the front door.

Grabbing a small clutch from out of her closet, (Y/N) rushes to the front door so as not to keep her date waiting. When she opens the door, she’s taken aback at how handsome Duncan looks in his suit and tie. Instead of the traditional white dress shirt, he’s chosen a black one that matches his suit. The effect of the all-black ensemble is maddening, and (Y/N) has to remember to take a breath when she sees him. What she’s not expecting is Duncan’s expression when he sees her. He unabashedly checks her out, eyes roaming her figure in the dress that perfectly accents her curves. His cheeks redden, and he shifts his weight back as if to restrain himself.

“(Y/N),” Duncan says her name lowly, “you look stunning.”

“Thank you. You don’t look so bad, either.”

There’s an odd confidence fluttering around in her chest as Duncan takes her hand and leads her downstairs, and it takes (Y/N) a moment to realize that she feels  _ sexy _ . This is new to her, and something she’s entirely unfamiliar with, but it’s difficult not to feel that way when the most gorgeous, most dangerous man she’s ever met is currently looking at her like he wants to pin her against a wall. The car parked outside is different from the last time Duncan gave (Y/N) a ride, but it’s still just as flashy as the previous one.

“Nice choice,” (Y/N) says approvingly, the Tesla barely making a sound as Duncan starts the car and pulls away from the curb.

“Oh, this old thing?” Duncan quips, smirking at (Y/N) when she jokingly rolls her eyes. “Thank you for doing this for me, I really do appreciate it.”

“It’s not like I had a choice in the matter, but regardless, you’re welcome.”

“I don’t want you to go in completely blind. Did you get a chance to look at the pictures that were enclosed with your dress?”

“Yeah, I’m assuming those are who you think will have information about your threat?”

“Exactly. What else do you know about who will be at the gala tonight?”

“Um, obviously the president. That one Scottish guy that tried to shoot you?” Duncan nods. “That’s about all I’ve got.”

“Both of those are correct. It’s important that we know where the president is at all times; she cannot know what is happening right under her nose again, or else the repercussions will be severe.”

“Wait, ‘again?’ So she knows about all of the organized crime in D.C.?”

“More like she’s complicit in it, and is even known to partake in it if it helps her out,” Duncan scoffs. “Frank Underwood was the exact same.”

“Holy shit,” (Y/N) says in disbelief, “I knew corruption ran deep in Washington, but not like  _ this _ .”

“The Coven will be here, too.”

The puzzle comes together in (Y/N)’s mind when Duncan says that. Zoe’s vague answers when asked what event she was buying a dress for, the fact that she even needed an extravagant dress in the first place, Madison’s reassurance that she would be “reimbursed” for the cost of the dress...that means that Duncan was right, and that Zoe and Madison really are a part of the Coven. Her hand tightens on the armrest, and she has to remember to keep breathing. “Will that...complicate my position, then?”

If Duncan does notice that (Y/N)’s having an inner crisis, he doesn’t say anything. “It shouldn’t, since people won’t know that we’re here together.”

Well, now (Y/N)’s  _ really _ freaking out. “What? Why not?”

“It will be a lot harder for you to get information if everybody knows that you’re with me tonight.” Pulling up to the venue where the Presidential Honors’ Gala is already taking place, Duncan parks his own car instead of letting the valet do it. “It’s going to be fine, (Y/N).”

“What am I supposed to do?”

“Lie,” Duncan says, like it’s the most obvious answer in the world.

“Okay, but what about if I do get information? What happens then?”

Duncan notices the panic on her face and puts his hand on top of hers to provide some amount of comfort. “That’s what these are for.”

(Y/N)’s about to question him when he reaches into the center console and pulls out two individual bags. “Are those...mics?” she asks, looking through the transparent plastic. 

“Yes. We will both be wired, and our conversations will be recorded.” Duncan hands a set to (Y/N), allowing her to loop the wire under her dress and up between her breasts. “May I?”

“Be my guest.”

He’s concentrated as he fixes the wire to where it won’t move around and isn’t able to be seen, his tongue  adorably just barely poking out between his lips. Affixing his own to the inside of his suit, he allows (Y/N) to return the favor and make sure his device isn’t visible.

“Are they recording right now?”

Duncan checks his phone, sighing before shaking his head. “No. My tech people seem to be woefully incompetent when it comes to establishing a wireless connection.”

“Give me your phone.” Although Duncan looks confused, he hands the phone to (Y/N). Almost immediately, she goes to work, tapping and typing when prompted. After a couple of minutes, she hands the phone back to Duncan. “Here.”

“What--did you connect it?” (Y/N) nods. “How did you know how to do that?”

“I like computers, and so I tried to learn as much as I could about a variety of technological things when I was in high school. One time I even managed to hack into the computer of a friend that lived across the country.” Duncan looks awed, and (Y/N) has to hide her prideful smirk at having a skill that Duncan doesn’t have. “So, should I go in first?”

“Ye-yeah, I think that would be best. I’ll be a few minutes behind you, but don’t act like you know me. These people that we’ll be interacting with can sense even the slightest bit of recognition that could blow the entire point of tonight.”

(Y/N) opens the car door, giving him a cheeky salute before mustering up all of the courage she has and heading to the entrance. Security hardly looks twice when she flashes them the plus one invitation that had been in the box containing her dress, and she makes her way into the ornately decorated hall without any sort of hassle. Once she’s able to take a breath and look around, she wishes that she hadn’t. There’s so many people of prominence here, people whose pictures she’s seen numerous times on TV or in the papers. The goddamn President of the United States is standing in the corner, looking radiant in her red dress and shaking hands like a queen. When a familiar voice calls her name, the confidence she had previously gathered shatters completely.

“Zoe!” (Y/N) says, turning around and acting like this is a wonderful surprise.

“Hi,” although she’s happy to see (Y/N), the worry in her eyes is evident. “What are you doing here?”

“It’s kind of a long story, but basically my uncle needed a plus one.”

“Your uncle?” Zoe asks, looking unconvinced.

“Yeah, the senator?” It’s a half-truth; her uncle is a senator, but he’s a state senator back home. Regardless, he’s been mentioned to Zoe before, and recognition dawns.

“Oh yeah! Where is he?”

“That’s what I’m trying to figure out. He ditched me as soon as we got here to do some networking.” Pretending to look for her uncle gives (Y/N) the perfect opportunity to peruse the faces that are in the ballroom a little longer. Right away, she can see two of the men whose pictures were included in the information she received: Mike Ricci, a Fortune 500 tech company COO who’s attempting to branch out into organized crime, and Jack Henry, the rumored illegitimate son of notorious Boston mob boss Will “Shorty” Henry. 

At the same time that (Y/N)’s deciding Mike Ricci will be her target (desperate to get into the inner circles, lots of money with which to bribe), Duncan makes his entrance. Almost immediately, all eyes are on him. It’s hard not to be drawn to the enigmatic man who runs one of the most successful companies in D.C. His cool, detached gaze sweeps across the room, barely lingering on the woman he’s become so fond of, who’s currently talking to Zoe Benson. He can only hope (Y/N) took his advice about lying to heart, but he can’t dwell on that for too long when Nicolas Corsetti of the Corsetti crime family is approaching him. Duncan lapses into the easygoing, yet tense conversation that seems to accompany all of the meetings with other members of organized crime, the entire time remaining acutely aware of the eyes of undercover FBI agents on them.

(Y/N) tries her best to not look at Duncan when he comes into the ballroom, trying to seem extra interested in what she’s talking about. When Ricci makes his way to the bar, however, she knows now is the time to act. “Hey, I’m gonna go get a drink. Do you want anything?”

Zoe shakes her head. “I’m good, but thanks. I’m actually gonna go do some networking.”

“Alright, send me a distress signal if you need help.” Walking to the bar, (Y/N) sidles up to Ricci’s left and waits patiently for the bartender. “A vodka soda, please.”

The bartender returns quickly with the drink, and (Y/N) smiles gratefully before taking a sip and glancing out of the corner of her eye. Sure enough, she’s garnering attention from her target. She’ll have to thank Duncan for the dress again; Ricci’s eyes are drawn to her cleavage, and she hides a smirk behind her glass. 

“Hi,” she greets.

“Hello. You’re a new face at these events.”

(Y/N) fakes a small laugh. “Do I really look that out of place here?”

“In a good way, I promise.” Ricci sets down his drink, holding his hand out. “I’m Mike Ricci.”

“(Y/N) (Y/L/N).” She wonders if she should have given a fake name, but there shouldn’t be any harm considering she’s supposed to have no knowledge of this world.

“And what brings you to this shark-infested tank tonight, (Y/N)?” Mike smiles, and she can see the appeal in a man like him. His thick, dark hair is swept back without looking too gelled, he looks like he spends a lot of time out in the sun, and his brown eyes twinkle when he smiles.

“I’m my uncle’s plus one. He’s a senator,” she says, sticking with the same lie.

“From what I’ve heard, that’s a dreadfully boring profession.”

“He doesn’t speak too fondly of it, but nights like these do give me a reason to dress up for once.”

“You really do look beautiful. It’s a shame you don’t have more reasons to dress up.”

Smiling bashfully, (Y/N) puts her hand on his upper arm. “So what do you do, if you’re not one of the boring senators?”

“Allow me to ask you to dance, and I’ll tell you.”

(Y/N) shrugs. “I suppose that can be arranged.” She slides her hand into his waiting one, leading her to the center of the room. A waltz is playing, and she silently thanks her first boyfriend for teaching her how to waltz in high school. 

Mike’s hand rests at her waist, his steps assured as he takes the lead. “I’m actually the Chief Operations Officer for EasTech.”

“Oh, I’ve heard of your company! You must be very proud of all of the accolades your business has received lately.” 

“It’s an honor to be recognized by the President for our work.”

“Does being a tech guru take up a lot of time?” (Y/N)’s a little astounded at how easy this role of femme fatale comes to her, batting her eyelashes as Mike spins her.

“More than I’d like, but I do have time for...other pursuits.” His posture stiffens, and (Y/N) sees him staring at a point behind her. When she turns her head to look, she’s met with the sight of Duncan looking like he’s ready to tear some throats out. The shadows cast upon his glowering face make his defined jaw look even more sharp and deadly, and her step falters when his icy blue eyes meet hers. Mike scoffs, and (Y/N) looks up at him.

“What’s wrong?”

“I knew Shepherd would be here, but it’s still not too pleasing to see his face.”

(Y/N) attempts to regain her airy confidence. “Uh oh, do I sense some tension?”

“You could call it that.” He lowers his voice conspiratorially. “You know, he’s allegedly involved in the mob.”

She rolls her eyes. “Come on, there hasn’t been organized crime since the 20th century.”

“That’s what they want everybody to believe.”

“So...Duncan Shepherd’s, like, a lackey in the mob?” (Y/N) knows she’s going to get so much shit for that when Duncan hears it later, but she’s hoping this ploy will work out.

“More like Duncan Shepherd’s the head of one of the most influential crime families in D.C.”

“Why are you upset with him? Is he attempting to take over your business?”

“By monopolizing the others in our industry, yes.” He shakes his head in disdain. “That’s why me and a few others are hoping to knock him off his pedestal.”

“You’re not going to  _ kill _ him, are you?”

“We’re not, but our associate might.” Looking at the spot where Duncan stood, she’s a little disappointed to see that he’s disappeared. On the bright side, that seems to mean that Mike thinks he’s safe to be talking about this. “You won’t go to the authorities with this, will you?”

“Please, you’d have to be stupid to do that. I understand the games that have to be played in order to reach the top.”

Mike smiles at her. “I knew there was something special about you, (Y/N).”

“Your associate sounds like they have a personal grudge against Duncan Shepherd,” (Y/N) moves back to the conversation.

“We’ve never actually met this mysterious benefactor of ours, but from what it sounds like, this grudge goes back years.”

She laughs, albeit a little nervously. “This sounds like something out of a movie. You really do lead quite the interesting life.”

“I’m glad you think so. If I haven’t scared you off with all of this talk, I’d like to take you on a date sometime soon.”

(Y/N)’s both flattered and at a loss for words, but before she can respond, there’s a hand on Mike’s shoulder. “Mr. Ricci.” By now, (Y/N) knows that voice like it’s her own.

Mike stops abruptly, (Y/N) crashing into his chest as a result. “Mr. Shepherd,” he stutters.

“Mind if I cut in? I couldn’t help but be intrigued by your lovely partner.” It’s clear from Duncan’s tone that Mike really doesn’t have a say in the matter; Duncan’s cutting in, whether he likes it or not.

“Of course.” Mike releases (Y/N) from his grasp, Duncan smoothly taking his place. “Come find me later, (Y/N).”

She nods, but her eyes are already glued to Duncan’s. “Hi darling,” Duncan mutters once Mike is out of hearing range, sweeping her into another waltz.

(Y/N) scowls, which was obviously not the reaction Duncan had been expecting. “Why the hell did you cut in? I was doing perfectly fine, and I almost had a name out of him!”

It’s as if Duncan had forgotten the reason for being here in the first place, emotions flicking through his eyes as easy as one leafs through the pages of a book; anger, confusion, followed by shame. “I didn’t like the way he was holding onto you. I thought he was going to try something.”

“I was more than willing to be groped a little for the sake of getting information.” The adrenaline has (Y/N) actually enjoying her role within Shepherd’s game, although she would never reveal that to him.

The pair glowers at each other, until finally, Duncan folds. “I was jealous, alright? Is that what you were wanting to hear?”

“Wait, what?”

If Duncan notices that she’s taken aback by his response, he doesn’t care. “I was jealous. His hands were all over you, and you were laughing at his jokes while he twirled you around like a scene from a goddamn Disney movie. I couldn’t handle seeing another man hold you like that when I should be the only one who gets that honor.”

“Are you forgetting what this is? We’re not together! I’m in your debt because you didn’t kill me. This is business, and that’s all.”

“I think we both know that’s not what this is anymore.”

The air is tense, electrified by the heavy emotions coming from both (Y/N) and Duncan. “Then...what is it?”

“I don’t know,” Duncan finally admits. “What I do know is that you enchant me, and you have from the beginning. I find myself constantly wanting to figure you out and know every little thing about you. I wonder what you’re doing when we’re not together, and I wonder if you feel the same as I do when we are.”

(Y/N) can’t seem to remember any word in the English language at the moment, but Duncan thankfully doesn’t give her the opportunity to respond. He leans his forehead against hers, slowing the dance to a sway as he looks at her earnestly.

“Come home with me,” he says lowly, as if the couples next to them will be eavesdropping on this conversation.

After a moment of contemplation, (Y/N) nods. “Okay.”


	8. Interlude

**Summary for the Chapter:**

> Duncan tries to engage in his classic self-sabotaging behavior, but (Y/N)’s not falling for it.

**Notes for the Chapter:**

> It’s the fic that everybody requests more of and nobody interacts with, Memento Mori! As the title for this chapter suggests, this is sort of the “break” between what could be considered acts 1 and 2. Feedback is always appreciated, my inbox is never closed, and likes and kudos make my world go round!
> 
> Follow me on Tumblr @7-wonders!

By the looks of the city, Washington D.C. appears to be silent. Looks, however, can be deceiving. For a seasoned resident of the metropolitan area, they know that this city is truly one that never sleeps. Within the hallowed halls of buildings that were built long before those walking them, and that will stand for years after those same feet cease to exist, deals are always being made. Politicians are much like bloodsucking vampires, although without sleeping during the day. They are ceaseless, always on a quest to advance themselves and their position at whatever cost.

Duncan Shepherd stands at the window of his penthouse bedroom, a weary king looking over his kingdom. He has earned this view, he knows, through his years of hard work to get to this position. Still, he can’t help but ponder all that he’s lost in order to get here. As the moonlight casts shadows on his face through the open curtain, Duncan knows that, for all the losses that he’s already faced, there will be countless more to come. For as long as he’s alive, loss will be a normal factor in his life.

“Dunc?” He turns around at the sound of a sleepy voice, finding (Y/N) blearily looking up at him from his bed. It’s a sight to behold, and it’s one that he would gladly experience time and time again. “Come back to bed.”

She looks every bit like she belongs here, in Duncan’s house, in his bed, in his arms. That’s exactly why he can’t look at her; not while knowing what he does, which is that she will undoubtedly experience loss in a magnitude which she never has before. If she’s lucky, maybe she won’t lose her own life, but people have a tendency of doing that when they associate themselves with Duncan Shepherd.

“Duncan,” she stirs him out of his thoughts, holding her hand out to him with a smile.

“I’ve decided to release you from our agreement,” Duncan says blankly, turning back towards the window.

“What?” (Y/N) sits up in bed, wide awake now.

“You’ve done what I asked of you, and there’s sufficient evidence to tie you to criminal activities should you have a lapse in judgement and go to the police. There’s no reason for you to be around anymore,” Duncan shrugs, trying desperately to act as though he’s nonchalant about what he’s just said.

“You want me to leave, then?”

“Yes.” The word tastes like battery acid on his tongue. He’s waiting to hear her cry, sniffling as she gathers up her clothes and leaves both his home and his life. Instead, all he hears is silence, which is somehow worse than what he had been expecting.

“I call bullshit.”

“Excuse me?”

“You heard me.” He waits for her to explode, but she’s frustratingly patient. “Look at me, Duncan.”

He tries to ignore the command, but (Y/N) is just as persistent as she is patient.

“We’re both adults, and we’re going to talk about this like adults. Now turn around so we can discuss this face-to-face.”

The pride that lies within Duncan makes him turn around. He still tries to avoid eye contact, but (Y/N)’s appeased for now.

“So what changed in the span of a few hours? Because I seem to remember you telling me that I enchant you and that you feel the need to figure me out.”

“You wouldn’t understand, you don’t know how my life works,” Duncan tries to insist.

“Yet, for better or for worse, you’ve made me a part of your life. Even the messy, illegal parts. I became part of your life from the moment you kissed me after we got shot at. So teach me. Help me to understand.” Although (Y/N)’s voice is even, one look at her eyes shows how much she’s silently pleading with Duncan. That one look, much like the first time they met and her fiery gaze was fixed upon him, melts any resolve he may have had.

“I don’t want to lose you,” Duncan mutters reluctantly.

“And by getting rid of me yourself, you assumed you would circumvent that?”

It sounds stupid now that it’s being said out loud, but that was exactly Duncan’s plan. “People that associate themselves with me die. Often in terrible, prolonged ways,” Duncan stresses.

“Your mom hasn’t died. Neither has Langdon.”

“The rare exceptions.”

(Y/N) rolls her eyes, annoyed at Duncan’s cynicism. “It’s fine to be wary, but for you to think that you’re going to be able to force me out of your life to ‘keep me safe’ is just stupid. I hate to tell you this, but you’re stuck with me now, whether you like it or not.”

“(Y/N)--”

“No! You keep talking about your feelings. That you don’t want to lose me, you need to have me close, and that you need to keep me safe, but you’re not giving any weight to my feelings.  _ I _ don’t want to lose you, Duncan. I feel safe when I’m with you, because I know that you’re safe. Even through all the danger and the secrecy, I can count on you to be my safe place. I know you think I should be scared of dying due to my relationship with you, but I’m not. Because I know that, even if I do die, I’ll die knowing that I got to love and be loved by you.”

Duncan’s lips part as he tries to find words amidst the shock, and (Y/N) laughs as she wipes the tears that have been threatening to spill.

“You’re a lot more transparent than you think. I knew you loved me when you called me the most infuriating woman you’ve ever met.”

“You’re wrong,” Duncan says softly. Before (Y/N) can angrily interject, he continues. “I’ve known I was in love with you since I picked you up for the weapons deal and saw the excitement on your face about the car I was picking you up in. I think I’ve been in love with you since I taught you how to fire a gun, I was just too thick-headed to recognize it.”

Slowly, as if pulled by a magnet, Duncan’s drifted closer to (Y/N). She manages to grab onto his hand, tugging him down next to her on the bed. Duncan’s arms go around her as she leans her head on his shoulder, finally feeling him relax for the first time since she woke to see his tense figure silhouetted against the window.

“I don’t want to be the reason you suffer,” Duncan admits.

“Unless you suddenly do a 180 and try to kill me, you won’t. We can’t control other people’s actions, Dunc, no matter how much we want to. I would face suffering regardless of whether or not we met; it’s a part of being alive.”

Duncan slips his fingers under (Y/N)’s chin, tilting her head up towards him. “I would torch this city to the ground if it meant you would never have to suffer.”

She smiles, gently kissing his lips. “A little overboard on the dramatics, but I appreciate the sentiment.”

“I love you, and I’m sorry for trying to push you away.”

“Even if there were no feelings involved and this was still strictly business, there’s no way you could get rid of me now. I’m far too invested in trying to figure out who has it out for you.”

Duncan smiles. “Impossible for me to not develop feelings for you.”

“Calm down Romeo, you don’t need to try and woo me when you already have me in your bed... _ naked _ ,” she whispers the last word in his ear, sending shivers down his spine.

With that, any residual sleepiness that either had been feeling disappears entirely as Duncan rolls (Y/N) onto her back so he can hover over her with one swift movement.


	9. What Kind of Monster Are You?

**Summary for the Chapter:**

> A month after Duncan and (Y/N)’s declarations of love, events seem to have settled down. That, of course, can’t last for too long.

**Notes for the Chapter:**

> I have no excuses. I’m a college student, and this is what you get when you follow me. Months between updates. Enjoy this chapter of Memento Mori!
> 
> Trigger Warnings in this chapter for crimes, weapons, and death.

“You’ve seemed a lot...happier lately,” Madison says one day out of the blue. She had met up with (Y/N) for a quick cup of coffee, back in town after having to jet away for a month merely a day after the gala. 

(Y/N) smiles bemusedly, taking a sip of her coffee. “Really?”

“Yeah, it’s sickening.” Madison grabs her bag, rifling through it and eventually producing a cigarette and a lighter.

“Madison!” (Y/N) admonishes, grabbing her wrist to stop her from lighting it. “You can’t smoke in here, this isn’t the sixties.”

“Ugh, fine.” Madison stands up abruptly, pulling (Y/N) up with her. “Let’s walk then, I need a cigarette.”

Madison looks at (Y/N) warily once they’re outside, rolling her eyes when she sees her getting ready to lecture her.

“I know, I’m going to get lung cancer and die a horrible death because I can’t kick the habit even though I know the risk,” she rattles off mockingly. “Lung cancer is the least of my worries at this point, babe.”

She scoffs. “You’re just miserable because neither you nor Zoe will make an actual move and commit to each other.” It had been almost  _ too _ easy to tell; Madison always runs away from her feelings, and Zoe’s aggressive perkiness was how she masked her sadness. 

Madison scowls, but the defeat in her eyes says otherwise. “Maybe so, but don’t deflect. Is it a guy? Or maybe a girl?”

Images pass through (Y/N)’s mind, of long nights and late mornings spent in the comfort of Duncan’s arms, small, secluded moments of intimacy (with the always-watchful eye of Duncan’s security). Rather than revealing what she’s actually been up to, she instead shrugs.

“Is it that guy who Zoe said you were talking with at the Presidential Gala?” (Y/N)’s blood runs cold, a sinking feeling in her chest telling her that Zoe and the Coven have caught on to her liaison with Duncan. “The CEO of EasTech?”

“Oh!” She laughs, relieved. “He was really nice, but nothing came of that.”

“It looked like Duncan Shepherd was pretty into you that night, from what I heard. He swooped you into a dance?”

(Y/N)’s face falls slightly, and she nervously clenches her first in the sleeve of her coat. “Yeah. He’s nothing special, though. Just another stuck-up rich socialite.”

Knowing that most of this has elements of truth makes it easier on (Y/N)’s conscience. Even though Duncan is nowhere near her, she wants to apologize to him and let him know just how special he is. Since he’s not, she’ll just keep her guilt to herself.

Madison puts her sunglasses on top of her head, which is how (Y/N) knows she’s about to be extremely serious. Of course, this can’t be good. (Y/N) cannot think of a single good thing that has ever come out of Madison removing her sunglasses when outside (she’s reminded of the time that some man had catcalled her, prompting Madison to take her sunglasses off and proceeding to verbally eviscerate said man until he stuttered out an apology).

“You need to be careful around somebody like Duncan Shepherd. He’s dangerous, okay?”

“It was just one dance! It’s not like I’m--” (Y/N) cuts herself off before she gets too upset. “Madison, I can promise you that I have no problems with Duncan Shepherd.”

“Okay. You just don’t know what he’s capable of, and I want you to be safe.”

“What exactly is he capable of? You’re not the first person to warn me of him, but I don’t know why.”

(Y/N) and Madison stare at each other, the former daring the latter to come up with some sort of explanation that won’t implicate Madison in the same circles as Duncan. (Y/N)’s phone, however, bails Madison out. 

“I have to go, I’m going to be late for work,” (Y/N) says.

“Text me when you get there safe.”

She nods, quickly hugging Madison before turning and walking down the street. Madison watches her until she disappears around the block before finally pulling out her phone and pressing the contact that she’s been calling increasingly often lately.

* * *

Duncan had given (Y/N) a key to his apartment barely two weeks into making things “official.” In his mind, it didn’t mean much; his circle is extremely small, and it means that (Y/N) always has a place to go (it certainly gave him a piece of mind to know that she could come to him whenever she wanted or needed, but that wasn’t something he felt inclined to share). Knowing that Duncan’s long hours don’t usually allow for him to cook meals, (Y/N) has started to take advantage of this access by cooking for him. It’s not as though he asked, or even requested, her to cook. Instead, it serves as a way to make food in a nice kitchen and not have to worry about leftovers.

It’s odd how fast a place can feel like home. Soft music plays on the speakers that Duncan’s had installed through his apartment, something classical that he’s fond of. (Y/N)’s hands easily find the locations of various ingredients and supplies that she needs, making it easy to lose herself in her thoughts. She comes back to herself when she hears the doorknob turn a couple of times, Duncan apparently having trouble with his keys. The door finally opens, and she calls out a greeting from around the wall that separates the entryway from the kitchen.

“I saw Madison today, and she was extremely suspicious of you,” she says to him, placing a lid on the pot and turning around. “I don’t know wha--”

Her sentence is cut off by a strangled squeak, coming face to face, not with Duncan, but with a stranger. A ski mask is pulled over his face, disguising all features except for his eyes, which look just as surprised to see (Y/N) as she is to see him.

“Uh...hi?”

“You’re not supposed to be here,” he says in a scratchy facade that is disguising his regular voice.

“Neither are you.” It’s all (Y/N) can think to say, eyes flashing down to the knife in the intruder’s hand. 

Both make eye contact with the other, simultaneously trying to decide their next move as well as the move that their opponent will make. (Y/N) runs, thanking Duncan for his open-concept apartment that gives her enough room to dodge the knife-wielding trespasser. He’s quick on her tail, hurdling over the couch and cutting the distance between them.

(Y/N) hears the sound of air whooshing behind her, crying out when she realizes she’s been cut by the knife. Thankfully he couldn’t reach her to stab her, and just barely got her on the back of the arm. Ducking down the hallway, she tips over the end table that houses a lamp. It’s not enough to fully stop the path of the attacker, but it’s enough to slow him down.

Locking herself in Duncan’s office, (Y/N) jams a chair under the doorknob. If this guy is one of Duncan’s enemies, there’s a good chance that he’ll be able to force his way into the room. But until then, the obstacle buys her time.

By some miracle, her phone had been in her pocket and not on the counter. She taps Duncan’s contact, eyes darting back and forth as the sounds of the attacker trying to bust open the door get louder and more forceful. Finally, he picks up.

“H--”

(Y/N) immediately cuts him off. “You need to get home,  _ now _ .”

“I’m driving home, what’s wrong?”

“Somebody with a knife broke into your apartment and is currently trying to kill me. I locked myself in your office, but I don’t think it’s going to hold much longer.”  
“Shit!” Duncan curses, flooring it and speeding from lane to lane. “There’s a gun strapped to the bottom of my desk chair. I need you to grab it, okay?”

She falls to her knees next to the desk, feeling along the bottom of the chair until her fingers hit cold metal. Yanking it out of the holster, she clicks the safety off and picks up the phone again. “I got it.”

“Good. You remember how to use it?”

“Yeah.”

“Okay, because I don’t know if I’m still a few minutes away from home. I’m going as fast as I can, but--”

“I understand. I love you, Duncan.”

“I love you too, but don’t say it like this is the last time we’re going to get to say it. You’re going to be okay.”

The door splinters open before (Y/N) can respond, the intruder kicking the chair across the room as he barges in. His eyes are wild and full of anger, but the gun being pointed at him stops him in his tracks.

“Don’t move,” (Y/N) commands, thankful that her hands aren’t shaking. Duncan’s voice is basically nonexistent from the phone, which is laying on the floor where (Y/N) dropped it to be able to properly aim the weapon.

“You threw quite the wrench in my plans. What are you, the maid?”

“What are you doing here?”

“No, you’re too familiar with this place to be a maid,” he continues, ignoring the question. After a moment, realization dawns on his face, and he laughs. “Don’t tell me, Duncan finally got himself a girlfriend? Oh, killing you will be even better than killing him.”

He walks forward, and (Y/N) cocks the hammer of the gun. “I said don’t move.”

“You’re not going to shoot me. You’re weak,” he continues to take steps after each word, (Y/N) pressing her back against the wall. “You don’t have the stomach to kill me. In fact, I might just keep you alive until Duncan gets home, make him watch as the life leaves your eyes--”

In fact, it’s (Y/N) who watches as the life leaves his eyes. It takes two shots to down him; the first caused him to stagger, but he continued to stumble forward until the second shot put him on his back. Distantly, she can hear noises that she retroactively realizes as Duncan’s voice from the phone, but it doesn’t register. Not as she stares at the body of the man she just shot.

Duncan has never felt as helpless as he does when listening to this intruder taunt (Y/N) with no way for Duncan to put a stop to it. When he hears shots, followed by eerie silence, he assumes the worst. The car is barely parked before Duncan throws himself out of the door, sprinting up the multiple floors of stairs until he reaches his apartment. The front door is wide open, and there’s food burning on the stove. Right now, none of that matters.

“(Y/N)!” Duncan shouts, feet pounding on the floor as he runs through the apartment. She can’t respond, still staring at the body of the man she just shot, but Duncan follows the sound of her ragged breaths into his study.

Physically, she looks okay. There’s a cut on the back of her arm, but she’s not going to die. Emotionally, however, she looks like she’s going into shock. The gun hangs loosely from her hand, and she doesn’t even look at Duncan as he grabs her shoulders.

“Sweetheart, are you okay?” Duncan asks, holding her tightly until she responds.

“I killed him,” (Y/N) finally says in a gasping breath, “Oh my god, I killed him.”

“Hey, stop that.” Duncan gently takes the gun from her hand, eyes locked on hers. “You didn’t kill him, okay? You only shot him.” 

Without looking, Duncan puts a bullet between the man’s eyes, (Y/N) jumping at the sound.

“There, I killed him.”

That seems to snap (Y/N) out of her shock, and she looks at Duncan with tear-filled eyes. “Duncan…”

“Shh, I know.” He wraps her in a hug before moving to set her down on the chair, darting out of the room before returning with a blanket. She didn’t even realize she was shivering until he placed it over her shoulders. “I’m so proud of you, you know that? You were so brave.”

“Do you know who he is?” (Y/N) asks. Duncan moves to the body, removing the ski mask and staring at him for a long moment.

“No, I don’t. Did he say anything about who he was with?”

She shakes her head. “All he said was that I wasn’t supposed to be here. I’m guessing you were his target.”

“You’re right, there’s nobody that would wish me dead that knows we’re together.”

“You know what I don’t get?” Duncan looks at her expectantly. “Why did he think a knife would be a good weapon to kill you with? I’m not a hitman, but I feel like a gun would be the easiest way to do it.”

“Hmm,” Duncan hums. “Why  _ did _ he use a knife?”

“Is this related to what Mike Ricci said? About the benefactor that apparently wants you dead?”

“Maybe.” 

An idea begins to form, although it could be extremely far-fetched. When Bill had died, there was a faction of the Shepherd empire that defected. They had known that Duncan had killed his uncle, and their loyalty to Bill had meant that they refused to work for Duncan. They hadn’t caused a problem since then, but maybe they had been plotting his demise all along.

“I have potential suspects in mind. Tomorrow, when you’re up for it, I would appreciate the use of your tech skills.”

“Of course. But...Duncan?”

“Yeah?”

“What are we supposed to do about the body currently on the floor?”


	10. Succession

**Summary for the Chapter:**

> The race to find whoever has it out for Duncan heats up, but answers may come too late for him.

**Notes for the Chapter:**

> Hello hello, welcome to Chapter 10 of Memento Mori! We’re definitely heating up here, and I wish I could see all of your faces when you’re reading this chapter. Um, as usual, let me know what you think, and if you really enjoyed it, kudos and comments are always appreciated.

“Duncan.”

The man in question looks up when his name is called, clicking out of the window of more sensitive information he had been looking at. Annette stands in the doorway of his office, a smile on her face and two cups of coffee in her hands.

“Do you have time for a chat with your mom?”

He nods, gesturing for her to come in. “Just close the door behind you.”

She hands him a coffee as she takes a seat in front of him, and he smiles gratefully. In the few months that he and (Y/N) had been officially dating, she had unexpectedly opened his eyes to the fact that his mother was likely just as much a victim of Bill’s abuse as he was. With those words in mind, Duncan had been slowly repairing his relationship with Annette, and even found her tolerable to be around.

“How have you been, mom? Busy?”

“I feel like I do nothing but twiddle my thumbs when I see how much work is on your schedule.”

“You’ve had those negotiations with the President,” Duncan points out.

“Yes, and those are certainly fulfilling. I do envy you, though. Some days I want nothing more than to conduct an interrogation again.”

Duncan laughs in disbelief. “There’s no way you used to interrogate people!”

“I did! I was good at it, too. I was also quite the markswoman, if I do say so myself.” She winks at him. “From what I’ve seen, that’s something you got from me.”

“Well then, I’ll be sure to keep you on speed dial next time somebody needs interrogating.”

“You had better let Michael know he has some competition in that field.”

“If he were here right now--”

Annette rolls her eyes. “Yes, I know, he’s big, bad, Langdon now. To me, he’ll always be that scrawny little teenager you brought home over break because his grandma had committed suicide and he had no family left.”

It’s true that Duncan and Michael Langdon have a history together. Michael had become Duncan’s roommate at Andover Prep after getting kicked out of the Hawthorne School for Exceptional Young Men. Although the two had a rough start as friends, they quickly bonded over teenage angst and feeling unwanted. Michael had disappeared for a couple of years after graduation before returning to D.C. Although he was ambiguous about where he had trained to become an assassin, Duncan was pretty sure that the lead he had found about his best friend being contracted for MI6 was true. Now, he was perfectly happy with being in the “private sector,” as they all cheekily referred to organized crime. It also helped that he was basically part of the family now--he should have known there was no way Annette wasn’t going to informally adopt his best friend upon learning of Michael’s shattered family life.

“Besides,” Annette continues, “at least he comes to see me for lunch.”

Duncan’s jaw drops playfully. “That’s because Michael’s a terrible cook! He knows he’ll get good food if he goes to your house.”

“Just promise me that you’ll come over soon, okay? Maybe you could bring her.” Annette points to the photo on Duncan’s desk that he had forgotten to hide away before his meetings this morning. 

It’s a picture of (Y/N) in the rain, smiling as she held her hand out to Duncan so that they could run to shelter together. In that moment, Duncan had been so enraptured by her that he felt the need to capture it physically. She had teasingly complained that she was going to get pneumonia all because he was “a sentimental sap,” but he had told her he would nurse her back to health if that were the case.

“What’s her name?” Annette prompts, realizing that Duncan’s not going to tell her anything unless she asks.

“(Y/N).”

“Pretty. Have you been seeing each other long?”

“We’ve been official for about three months now, but we’ve known each other for seven.”

Annette’s eyes glow. “You haven’t had a relationship this long since college!”

Duncan rolls his eyes, but knows his mom is just pointing out what’s true. “Yes well, she’s...special.”

“Does she know?”

It goes unspoken what she means. “Funny story, actually.”

“Duncan, tell me you did not blackmail this poor girl.”

“I had no choice! She saw me,” he lowers his voice, “dispose of Kai Anderson. I couldn’t just let this random woman walk free.”

“So what changed? What made her different from the others who have served as collateral?”

“(Y/N)’s smart, so smart. And she doesn’t care about the money, or the power, or my status. I’ve seen her stare death in the eye completely unflinching. Remember when I had to have that man removed from my house?” Annette nods. “He was looking for me, but he found (Y/N) instead.”

“Is she okay?”

“Believe it or not, she actually shot the guy.”

Annette laughs in disbelief. “Seems like you’ve found yourself a keeper, Duncan.”

“I certainly think so.” Duncan pulls up the window on his computer that he had previously been looking at, gesturing for his mother to look at the screen. “(Y/N)’s actually pretty good with technology. She managed to get the security camera footage from outside of my place, and she enhanced the footage enough that we have a pretty good view of what’s happening.”

Duncan plays the footage, which is zoomed in to show the man walking into Duncan’s apartment. Clicking another key, a different camera shows a new angle in which a black SUV drops off the would-be killer. Both only having seen the man dead, mother and son study his angular face and dark eyes to see if they recognize him. 

“I don’t know who he is. I got the ID back from our guy that works in the coroner’s office, but the name isn’t one that’s familiar to me.” Duncan starts looking through his files to find the one that he had mentioned, but Annette’s still stuck staring at the screen.

“That almost looks like Kenneth,” she mutters.

“Kenneth?”

“Mhm, one of your uncle’s guys.”

“That works with the theory that (Y/N) and I have, that some of those loyal to Bill are trying to get rid of me for revenge.”

“You really think they would kill you?”

“They know what I did to him, Mom. Of course they want me dead.” Duncan finds the file he was looking for, opening it up and reading the information inside. “Kenneth Li, 52 years old, former financial advisor to Bill Shepherd.”

Annette glances at Duncan. “Who trained a financial advisor to become a hitman?”

“Somebody who knows enough about what happened that night to know that coming at me with a knife is irony at its finest.”

“I’m assigning you some extra security until we can figure out who’s running this operation,” Annette says finally, hand going for the phone on her lap.

“No!” Duncan grabs her hand, stopping her from contacting anybody. “That will just make them more suspicious, and more than likely they’ll try to kill me faster. Besides, I have Michael. He can tail me for a couple of days, if that will make you feel better.”

“I’d feel better having more than one set of eyes on you.”

“But he’s a very capable set of eyes,” Duncan points out.

“You’re sure that this is the best move?”

“Absolutely.”

She sighs. “Alright. I just want you to be safe, okay? I don’t know what I would do if I lost you.”

“Don’t worry, I’m not going anywhere.”

* * *

(Y/N)’s deep into a rabbit hole of information at this point. Bank statements, meeting minutes, surveillance footage, newspaper articles, and even autopsy reports abound at this point. Every time she seems to have a hint of where this might be leading, it all seems to be swept away by a new clue wiping away the prior theory. The only thing that’s certain is that every person of interest, every event, leads back to one organization: Umbra Inc. She has no clue what the company is, what they do, and let alone who they’re run by. Their president and CEO is only listed by their initials, W.S.

“C’mon, Shakespeare, show me who you are,” (Y/N) mutters. She’s been trying to track down W.S. for hours now, and has taken to referring to them as the Bard in order to try and not go crazy staring at a screen. “Aha!”

A bank statement shows the physical address for Umbra Inc., located on the other side of D.C. That’s definitely a start, considering they seem to have no presence online or in person. It takes a few minutes, but (Y/N)’s able to find a couple of security cameras that face their building. Even better is when she gets into the cameras inside their building. She allows herself a little pat on the back for that; it’s been three days since she found the mysterious organization that seems to be the center of everything, and this seems to be the first big break since then.

At first, there’s nobody on the cameras that raises any eyebrows. Then, she sees the man who she’s been tracking, the one whose autopsy report she’s read inside and out. The image of Kenneth Li enters the building on the day of his death, and (Y/N) quickly pulls up camera after camera to follow him through the office. She loses him for a bit when he takes the elevator, but catches him again when he exits on the top floor. From what she knows about business, this is usually where the CEO’s office is located, which means it’s highly likely that Li is meeting the elusive W.S.

Sure enough, the door at the end of the hallway opens and a man sticks his hand out to greet Li. He’s deliberately trying to stay out of sight of the camera that sits in the corner closest to his office door, but has failed to take into account just how high-tech the security system is. Two more camera angles show his face, which is blurred until she zooms in and enhances the image a couple times. Now, she can see him clearly. Unfortunately, she has no clue who he is.

“More research, I guess,” (Y/N) mutters, pulling up the list of known associates who broke away from the Shepherd Freedom Foundation after Duncan’s uncle’s death.

It takes almost an hour to look through the entire list, with no sort of match to the figure currently paused on (Y/N)’s screen. She groans in frustration, banging her hand on Duncan’s desk. You would think matching two faces together would be easy, but that doesn’t seem to be the case here. Deciding to start from the beginning, she pulls up the report of that night where everything in Duncan’s world shattered. It’s painful every time she reads it; Duncan’s shock, Annette’s sobs, and the pool of blood surrounding Bill all make for a queasy reading experience. The crime scene photos also aren’t fun to look at, and she’s sure that she’ll be seeing those in her sleep for a long time.

“Wait a minute,” (Y/N) says suddenly, sitting up in the chair. Looking from the picture on the left side of the screen, to that of the enhanced camera footage on the right side. Repeating that a couple more times in disbelief, it finally clicks that she’s seeing what she thinks she’s seeing. 

(Y/N) puts the needed information into a file before sending it to Duncan’s phone, picking up her own phone and calling him. To her chagrin, he doesn’t pick up. It’s not too surprising, considering it’s only 4:30 and he’s probably doing actual legal business right now, but she needs him to know as soon as possible.

“Duncan,” she says as soon as the voicemail machine beeps, “call me back when you can, I think I might have figured all of this out. I sent the information to your phone, so take a look at that first. It sounds and looks crazy, I know, but trust me on this.”

Little does she know that her call, as well as her messages, will go unanswered. Mere hours after assuring his mother that he would be okay until Langdon got back, he had been on his way to a meeting with a potential new business partner working under the name Umbra Inc. The last thing Duncan remembered was walking into the building where Umbra was housed; now here he is, waking up some place completely unfamiliar. 

Duncan only allows himself to panic for a second before getting his emotions back under control. Everything in kidnapping crisis training says not to freak out, but now, his first time as kidnappee and not kidnapper, he can see why people panic so easily. He has no clue where he is, and it’s too dark to see what sort of a room he’s being held in. He’s on the floor, his arms chained together with the chain looped around a radiator.

When a door finally opens and a thin beam of light shines in the room, Duncan’s already preparing to charmingly ask his captors of their demands. After all, he’s an important political figure. More than likely, whoever kidnapped him wants money, which his family has more than enough of. 

“Long time, no see. What’s it been, five years now?” Duncan furrows his eyebrows. He knows that voice, but why can’t he think of who it belongs to?

“I can assure you that, whatever it is you want, my family can provide for you. Nobody needs to get hurt.”

“I know all about what your family can provide, Duncan, but it’s not money that I want. It’s you.”

“Me? What kind of motive do you have?” He knows he’s gotten a bit ahead of himself with that when he gets slapped across the face, considering one of the top rules of being kidnapped is not pissing off your abductor.

“And here I thought five years would give you enough time to grow a brain, considering the good things I’ve heard about you. Guess not, though. What I want from you is simple.” Shoes tap on the floor as the man walks across the room and flicks a switch, bathing the room in bright light. Duncan’s eyes take a moment to adjust, and he blinks furiously to clear his sight. “I want revenge for everything you took from me.”

Duncan stares, mouth slightly agape. He feels like he’s seeing a ghost, and in reality, he kind of is, considering the man standing in front of him is supposed to be dead and buried. “Uncle Bill?”


End file.
